HUE026195T2 - 4-amino-5-fluoro-pyrimidine derivatives as fungicides - Google Patents

4-amino-5-fluoro-pyrimidine derivatives as fungicides Download PDF

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HUE026195T2
HUE026195T2 HUE09704708A HUE09704708A HUE026195T2 HU E026195 T2 HUE026195 T2 HU E026195T2 HU E09704708 A HUE09704708 A HU E09704708A HU E09704708 A HUE09704708 A HU E09704708A HU E026195 T2 HUE026195 T2 HU E026195T2
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alkyl
ring
groupe
phenyl
optionally substituted
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HUE09704708A
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Hungarian (hu)
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Zoltan Benko
Timothy Boebel
Nneka Breaux
Kristy Bryan
George Davis
Jeffrey Epp
Beth Lorsbach
Timothy Martin
Kevin Meyer
Bassam Nader
W Owen
Mark Pobanz
James Ruiz
Frisby D Smith
Michael Sullenberger
Jeffery Webster
Chenglin Yao
David Young
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Dow Agrosciences Llc
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
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    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
    • A—HUMAN NECESSITIES
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    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
    • A—HUMAN NECESSITIES
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    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
    • A01N47/44—Guanidine; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds
    • A01N57/32—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds containing heterocyclic radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Description

• RUIZ, James Westfield IN 46074 (US) • SMITH, Frisby D.
Dixon CA 95620 (US) • SULLENBERGER, Michael Westfield IN 46074 (US) • WEBSTER, Jeffery New Palestine IN 46163 (US) • YAO, Chenglin Westfield IN 46074 (US) • YOUNG, David Carmel IN 46033 (US) (74) Representative: Weickmann &amp; Weickmann Postfach 860 820 81635 München (DE) (56) References cited: EP-A- 0 139 613 EP-A- 0 332 579 GB-A- 1 461 184 US-A- 3 868 373 • JAWORSKI, ANDRZEJ ET AL: "Infrared spectra and tautomerism of 5-fluorocytosine, 5-bromocytosine and 5-iodocytosine. Matrix isolation and theoretical ab initio studies" JOURNAL OF MOLECULAR STRUCTURE , 223, 63-92 CODEN: JMOSB4; ISSN: 0022-2860, 1990, XP002523451 • BIRESSI M GABRIELLA ET AL: "Some 5-fluorosulfanilamidopyrimidines" GAZZETTA CHIMICA ITALIANA, SOCIETA CHIMICA ITALIANA, ROME, IT, vol. 93, no. 10, 1 January 1963 (1963-01-01), pages 1268-1278, XP009115256 ISSN: 0016-5603
Description
Field of the Invention [0001] This present disclosure is related to the field of 5-fluoro pyrimidines and their derivatives and to the use of these compounds as fungicides.
[0002] EP 0 139613 discloses N-(2-nitrophenyl)-4-aminopyrimidine derivatives as fungicides for agricultural use.
[0003] EP 0 332 579 discloses isonicotinic acid amides substituted by heterocycles as fungicides for agricultural use.
[0004] Thus, EP 0 139 613 and EP 0 332 579 both relate to compounds containing two cyclic groups which are useful as fungicides for agricultural use.
[0005] U.S. 3,868,373 relates to chemotherapeutically active cytosine nucleosides. Specifically, 4-amino-5-fluoro-2-trimethylsilyloxypyrimidine is mentioned as astarting compound which is to be condensed with particular sugar derivatives to form the corresponding cytosine nucleosides which are chemotherapeutically active.
[0006] Biressi et al. discloses 2-methoxy-4-amino-5-fluoro-pyrimidine which exhibits pharmacological effects, e.g. as an antitumor agent or antibiotic.
[0007] U.S. 3,868,373 and Biressi et al. both relate to a different technical field. Therefore, the compounds disclosed therein have been excluded from the scope of the present invention by way of a disclaimer.
[0008] GB 1 461 184 relates to a process for the manufacture of 5-fluorocytosine, wherein 2-ethoxy-4-amino-5-fluor-opyrimidine is used as a starting compound and further subjected to hydrolysis in order to obtain 5-fluorocytosine. As the specifically disclosed compound 2-ethoxy-4-amino-5-fluoropyrimidine is not used by itself but only as a starting compound for a further reaction, also this compound has been excluded from the scope of the present invention byway of a disclaimer.
Background and Summary of the Invention [0009] Fungicides are compounds, of natural or synthetic origin, which act to protect and cure plants against damage caused by agricultural relevant fungi. Generally, no single fungicide is useful in all situations. Consequently, research is ongoing to produce fungicides that may have better performance, are easier to use, and cost less.
[0010] The present disclosure relates to 5-fluoro pyrimidine compounds and their use as fungicides. The compounds of the present disclosure may offer protection against ascomycetes, basidiomycetes, deuteromycetes and oomycetes.
[0011] The scope of the invention is defined by the appended claims. One embodiment of the present disclosure includes compounds of Formula I wherein R1 is -N(R3)R4;
R2 is -OR21; R3 is: H; R4 is: H; R8 is independently C^Cg alkyl, C-pCg haloalkyl, amino, C^Cg alkylamino, C2-C6 dialkylamino, phenyl optionally substituted with 1-3 R30, or a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11; R11 is independently halogen, CrCg alkyl, CrC6 haloalkyl, CrC6 alkoxy, CrC6 haloalkoxy, CrC6 alkylthio, CrC6 haloalkylthio, amino, C.|-Cg alkylamino, C2-C6 dialkylamino, C2-C6 alkoxycarbonyl, or C2-C6 alkylcarbonyl,; R20 is independently halogen, cyano, nitro, amino, C^Cg alkoxyalkoxy, C1-C6 alkyl, C1-C6 haloalkyl, C-pCg hydroxyalkyl, C2-C6 allcoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, hydroxyl, C-j-Cg alkoxy, CrCg haloalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C3-C6 allcynyloxy, C3-C6 haloalkynyloxy, C^Cg alkylthio, C^Cg haloalkylthio, C-pCg alkylsulfonyl, 0Γ06 haloalkylsulfonyl, C2-C6 alkenylthio, C2-C6 haloalkenylth-io, C2-C6 haloalkenylsulfonyl, C3-C6 alkynylthio, C3-C6 alkynylsulfonyl, C3-C6 haloalkynylsulfonyl, CrC6 alkylamino, C2-C8 dialkylamino, C3-C8 dialkylaminocarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C3-C6 trialkylsilyl, 2-[(E)-methoxyimino]-N-methyl-acetamidyl, phenyl, benzyl, benzyloxy, phenoxy.ora 5-or 6- membered heteroaromatic ring wherein each phenyl, benzyl, benzyloxy, phenoxy, or 5- or 6- membered heteroaromatic ring may be optionally substituted with 1-3 substitutents independently selected from R31; R21 is:
CrC14 alkyl;
CrC6 haloalkyl; C2-C4 alkenyl,; C2-C4 haloalkenyl; C3-C4 alkynyl; C3-C4 haloalkynyl; phenyl, naphthyl, or tetrahydroquinolinyl each optionally substituted with 1-3 R20; -(CHR22)mR23; -(CHR24)mC(0)0R25; -(CHR24)mC(0)R26; -(CHR24)mC(0)N(R27)R28; -(CHRz4)mOR29; -(CHR24)mSR29 -(CHR24)mN(R27)R28; -C(=0)R32; -N=C(R32)(R36); -NR25C(=0)0R25 -Si(R8)3; -S02R33; C2-C6 alkoxy carbonyl; C2-C6 alkylaminocarbonyl;. C2-C6 alkylcarbonyl; sugars selected from the group consisting of beta-D-glucose-tetraacetate, rhamnose, fructose, and pentose; or a 5- or 6- membered heteroaromatic ring selected from the group consisting of furanyl, pyridinyl, pyridinyl-N-oxide, pyrimidinyl, pyridazinyl, pyrazinyl, pyrazolyl, thiazolyl, triazinyl, thiadiazolyl, oxazolyl, triazolylorisoxazolyl wherein each 5- or 6- member heteroaromatic ring may be optionally substituted with 1-5 R20; wherein m is an integer from 1-3; R22 is independently: H; halogen; cyano; nitro;
CrC6 alkyl;
CrC6 haloalkyl; phenyl or benzyl optionally substituted with 1-3 R20;
CrCg hydroxyalicyl; C2-C6 alkoxylalkyl; C3-C6 haloalkynyl; C2-C6 alkenyl; C2-C6 haloalkenyl; C3-C6 alkynyl; C^Cg alkoxy;
Ci-C6 haloalkoxy; C.|-Cg alkylthio; C.|-Cg alkylamino; C2-C8 dialkylamino; C3-C6 cycloalkylamino; C4-C6 (allcyl)cycloalkylamino; C2-C6 alkylcarbonyl; C2-C6 alkoxycarbonyl; C2-C6 alkylaminocarbonyl; C3-C8 dialkylaminocarbonyl; C3-C6 trialkylsilyl; ring-fused heteroaromatic rings selected from the group consisting ofbenzothiophenyl, quinolinyl, isoquinolinyl, thieno[2,3-b]pyridyl, 1-methyl-1 H-thieno[2,3-c]pyrazolyl, and benzoimidazolyl, wherein each of the rings may be further substituted with 1-3 R20; or a 5- or 6- membered heteroaromatic ring selected from the group consisting of furanyl, pyridinyl, pyridinyl-N-oxide, pyrimidinyl, pyridazinyl, pyrazinyl, thiazolyl, triazinyl, thiadiazolyl, oxazolyl, iso-xazolyl, triazolyl and thienyl; R23 is: H; halogen; C^Cg alkyl; C^Cg haloalkyl; C2-C6 dialkylamino; phenyl optionally substituted with 1-5 R20; ring-fused heteroaromatic rings selected from the group consisting of benzothiophenyl, quinolinyl, isoquinolinyl, thieno[2,3-b]pyridyl, 1-methyl-1 H-thieno[2,3-c]pyrazolyl, benzofuranyl and benzoimidazolyl, 2,3-dihydro-benzo-furan-2-yl, 4-methyl-4H-thieno[3,2-b]pyrrol-5-yl, 1-methyl-1 H-indol-5-yI, imidazo[1,2-a]pyridin-2-yl, imidazo[2,1-b]thiazol-6-yl, benzothiazol-2-yl, benzo[b]thiophen-7-yl, and-1-methyl-1 H-indazol-3-yl, wherein each of the rings may be further substituted with 1-3 R20; naphthyl; benzo[1,3]dioxolyl; pyrrolidinonyl; oxetanyl; C-|-Cg alkylthio optionally substituted with 1-5 R20; a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11; or a 5- or 6- membered heteroaromatic ring selected from the group consisting of furanyl, pyridinyl, pyridinyl-N-oxide, pyrimidinyl, pyridazinyl, pyrazinyl, pyrazolyl, thiazolyl, triazinyl, thiadiazolyl, oxazolyl, isoxazolyl, triazolyl, imidazolyl, thiophene-2-yl and thiophen-3-yl wherein each heteroaromatic ring may be optionally substituted with 1-3 R20; R24 is H, CrC6 alkyl, CrC6 alkoxy, benzyl, or phenyl wherein each of the benzyl or phenyl may be optionally substituted with 1-3 R20; R25 is H, CrC6 alkyl, phenyl or benzyl optionally substituted with 1-3 R20; 26 js. R ls- H;
CrC6 alkyl; C^Cg alkoxy; phenyl optionally substituted with 1-3 R20; or a 5- or 6 membered heteroaromatic ring selected from the group consisting of furanyl, pyridinyl, pyridinyl-N-oxide, pyrimidinyl, pyridazinyl, pyrazinyl, thiazolyl, triazinyl, thiadiazolyl, oxazolyl, triazolyl and isoxazolyl; R27 and R28 are independently: H; C-pCg alkyl; benzyl or phenyl wherein each of the benzyl or phenyl may be optionally substituted with 1-3 R20;or a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11; R29 is: H; G-|-Gg alkyl; C^Cg haloalkyl; C^Cß alkoxyalkyl; C2-C6 alkylcarbonyl; benzyl or phenyl wherein each of the benzyl or phenyl may be optionally substituted with 1-3 R20; or a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11; R30 is independently halogen, cyano, nitro, CrC6 alkyl, C-j-Cg haloalkyl, CrC6 hydroxyalkyl, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C6 alkenyl, C2-C6 haloallcenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, hydroxyl, C^Cg alkoxy, C^Cg haloalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 haloalkynyloxy, C^Cg alkylthio, C^Cg alkylsulfonyl, C^Cg haloalkylsulfonyl, C2-C6 alkenylthio, C2-C6 haloalkenylthio, C2-C6 haloalkenylsulfonyl, C3-C6 alky-nylthio, C3-C6 alkynylsulfonyl, C3-C6 haloalkynylsulfonyl, C-j-Cg alkylamino, C2-C8 dialkylamino, C3-C8 dialkylaminoc-arbonyl, C3-C6 trialkylsilyl, thiazolyl, phenyl, pyrimidinyl, or pyridyl, wherein the thiazolyl, phenyl, pyridyl, or pyrimidinyl may be optionally substituted with 1-3 R20; R31 is independently halogen, cyano, nitro, C^Cg alkyl, C^Cg haloalkyl, C-pCg hydroxyalkyl, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, hydroxyl, C^Cg alkoxy, C-j-Cg haloalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 haloalkynyloxy, C-pCg alkylthio, C-j-Cg alkylsulfonyl, C-|-Cg haloalkylsulfonyl, C2-C6 alkenylthio, C2-C6 haloalkenylthio, C2-C6 haloalkenylsulfonyl, C3-C6 alky-nylthio, C3-C6 alkynylsulfonyl, C3-C6 haloalkynylsulfonyl, C.|-Cg alkylamino, C2-C8 dialkylamino, C3-C8 dialkylaminoc-arbonyl, or C3-C6 trialkylsilyl; R32 is independently:
Ci-Cg alkyl, C1-C6 haloalkyl, Ci-Cg hydroxyalkyl, C2-C6 allcoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, hydroxyl, CrC6 alkoxy, CrCg haloalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 haloalkynyloxy, CrC6 allcylthio, C^Cg alkylsulfonyl, C-pCg haloalkylsulfonyl, C2-C6 alkenylthio, C2-C6 haloalkenylthio, C2-C6 haloalkenylsulfonyl, C3-C6 alkynylthio, C3-C6 alkynylsulfonyl, C3-C6 haloalkynylsulfonyl, C^Cg alkylamino, C2-C8 dialkylamino, C3-C8 dialkylaminocarbonyl, C3-C6 trialkylsilyl; phenyl wherein the phenyl ring may be optionally substituted with 1-3 R20; or a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11; R33 is independently:
CrCg alkyl, C.|-Cg haloalkyl, phenyl or thienyl optionally substituted with 1-3 R20; or a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11; R34 is: C-j-Cg alkyl, CrCg haloalkyl, C2-C6 alkoxyalkyl, CrC6 alkylamino; or a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11; R35 is: C|-C6 alkyl, C2-C6 alkylcarbonyl; or a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11; R36 is H, cyano, C1-C6alkyl, C1-C6 alkoxy, benzyl, or phenyl wherein each of the benzyl or phenyl may be optionally substituted with 1-3 R20; alternatively R32 and R36 may be taken together to form: a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11; and R37 is independently: H, halogen, or phenyl optionally substituted with 1-5 R20;
CrC6 alkyl, CrC6 haloalkyl, hydroxyl, CrC6 alkoxy, or CrC6 haloalkoxy; or a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11, with the proviso that the compound is not 4-amino-5-fluoro-2-tri-C1-C7-alkyl-silyloxypyrimidine, 2-ethoxy-4-amino-5-fluoropyrimidine or 2-methoxy-4-amino-5-fluoropyrimidine.
[0012] Also disclosed are compounds of Formula I:
wherein R1 is -N(R3)R4; R2 is -OR21; R3 is: H; C1 -Cg alkyl optionally substituted with 1- to 3 R5; C2-C6 alkenyl optionally substituted with 1-3 R5; a 5- or 6- membered heteroaromatic ring selected from the group consisting of furanyl, pyridinyl, pyridinyl-N-oxide, pyrimidinyl, pyridazinyl, pyrazinyl, thiazolyl, triazinyl, thiadiazolyl, oxazolyl, isoxazolyl, triazolyl, each heteroaromatic ring being optionally substituted with 1-3 R30; imidazole fused with an aromatic or heteroaromatic ring selected from the group consisting of benzene, oxazole, isoxazole, furán, thiazole, pyrimidine, pyridine, pyrrole, pyrazine, thiophene, each aromatic or heteroaromatic ring being optionally substituted with 1 to 3 R30; benzo[1,3]dioxolyl; 3H-isobenzofuran-1-onyl; cyano; C3-C6 alkynyl optionally substituted with 1-3 R5; -C(=0)R6; -C(=0)0CH2C(=0)R8; -C(=S)R6; -C(=S)NHR8; -C(=0)N(R8)R10; -OR7; -P(0)(0R15)2; -S(0)2R8; -SR8; -Si(R8)3; -N(R9)R10; -N=C(R15)R16; -(CHR22)mR37; -(CHR24)OR29; or -C(=NR16)SR16; wherein m is an integer from 1-3; R4 is: H;
CrC6 alkyl, optionally substituted with 1-3 R5; -C(=0)R6; or -C(=0)N(R8)R1°; alternatively R3 and R4 may be taken together to form: a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11; =C(R12)N(R13)R14; =C(R13)(R14); =C(R15)OR15; =S(R34)2 ; or =NR35; R5 is independently halogen, C-pCg alkyl, C.1-C4 haloalkyl, C.1-C4 alkoxy, haloalkoxy, C.1-C4 alkylthio, CA-C4 haloalkylthio, amino, C-j-Cg alkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C2-C6 alkylaminocarbonyl, -OH, N-methyl piperazine or C3-C6 trialkylsilyl; R6 is independently H, C-j-Cg alkyl, C-j-Cg haloalkyl, C-j-Cg alkoxy, C-j-Cg haloalkoxy C2-C6 alkoxycarbonyl, C1-C4 alkoxy-alkoxy, C2-C6 alkylaminocarbonyl; 1-benzo[1,2,3]thiadiazol-7-yl, thiazolyl, benzyl, phenyl, phenoxy, or benzyloxy wherein the thiazolyl, benzyl, phenyl, phenoxy, or benzyloxy may be optionally substituted with 1-3 R20, a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11; R7 is H, Ci-Cg alkyl, C2-C6 alkenyl, 0Γ05 haloalkyl, benzyl which may be optionally substituted with 1-5 R20, CHR18C(0)0R19, or a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11; R8 is independently CrC6 alkyl, CrC6 haloalkyl, amino, C^Cg alkylamino, C2-C6 dialkylamino, phenyl optionally substituted with 1-3 R30, or a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11; R9 is H, CrC6 alkyl CrC6 haloalkyl, -C(=0)R17, or phenyl optionally substituted with 1-3 R20, R10 is H or CrC6 alkyl, CrC6 haloalkyl, or phenyl optionally substituted with 1-3 R20; R11 is independently halogen, CrC6 alkyl, CrC6 haloalkyl, CrC6 alkoxy, C^Cg haloalkoxy, Cr C6 alkylthio, CrC6 haloalkylthio, amino, CrC6 alkylamino, C2-C6 dialkylamino, C2-C6 alkoxycarbonyl, or C2-C6 alkylcarbonyl; R12 is H or CyC4 alkyl; R13 and R14are independently H, cyano, -OH, CVC4 alkyl, 0Γ06 alkoxy, C2-C6, alkylcarbonyl, phenyl, or benzyl wherein the phenyl or benzyl may be optionally substituted with 1-3 R20; alternatively R13 and R14 may be taken together to form: a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11, or 3,4-dihydro-1 H-isoquinolin-2-yl; alternatively R12 and R13 may be taken together to form: a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11; R15 is H or C^Cg alkyl; R16 is H, Ci-Cg alkyl, or phenyl optionally substituted with 1-3 R20; alternatively R15 and R16 may be taken together as -(CH2)4- or -(CH2)5- ; R17 is H, CrC6 alkyl, CrC6 haloalkyl, CrC6 alkoxy, phenyl, phenoxy, or benzyloxy wherein each ring may be optionally substituted with 1-3 R20; R18 is H, C-pCg alkyl, or C-pCg haloalkyl; R19 is H, C-|-Cg alkyl, C.|-Cg haloalkyl, or benzyl; R20 is independently halogen, cyano, nitro, amino, CrCg alkoxyalkoxy, C-j-Cg alkyl, C-j-Cg haloalkyl, CrC6 hydroxyalkyl, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, hydroxyl, CrC6 alkoxy, C-pCg haloalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 haloalkynyloxy, C-pCg alkylthio, C-pCg haloalkylthio, C.|-Cg alkylsulfonyl, C.|-Cg haloalkylsulfonyl, C2-C6 alkenylthio, C2-C6 haloalkenylthio, C2-C6 haloalkenylsulfonyl, C3-C6 alkynylthio, C3-C6 alkynylsulfonyl, C3-C6 haloalkynylsulfonyl, C^Cg alkylamino, C2-C8 dialkylamino, C3-C8 dialkylaminocarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C3-C6 trialkylsilyl, 2-[(E)-meth-oxyimino]-N-methyl-acetamidyl, phenyl, benzyl, benzyloxy, phenoxy.ora 5-or 6- membered heteroaromatic ring wherein each phenyl, benzyl, benzyloxy, phenoxy, or 5- or 6- membered heteroaromatic ring may be optionally substituted with 1-3 substitutents independently selected from R31; R21 is: H; C-|-C-|4 alkyl; C-pCg haloalkyl; C2-C4 alkenyl; C2-C4 haloalkenyl; C3-C4 alkynyl; C3-C4 haloalkynyl; phenyl, naphthyl, or tetrahydroquinolinyl each optionally substituted with 1-3 R20; -(CHR22)mR23; -(CHR24)mC(0)0R25; -(CHR24)mC(0)R26; -( C H R24) mC(0)N(R27)R28; -(CHR24)mOR29; -(CHR24)mSR29 -(CHR24)mN(R27)R28; -C(=0)R32; -N=C(R32)(R36); -NR25C(=0)0R25 -Si(R8)3; -S02R33; C2-C6 alkoxy carbonyl; C2-C6 alkylaminocarbonyl; C2-C6 alkylcarbonyl; sugars selected from the group consisting of beta-D-glucose-tetraacetate, rhamnose, fructose, and pentose; or a 5- or 6- membered heteroaromatic ring selected from the group consisting of furanyl, pyridinyl, pyridinyl-N-oxide, pyrimidinyl, pyridazinyl, pyrazinyl, pyrazolyl, thiazolyl, triazinyl, thiadiazolyl, oxazolyl, triazolyl or isoxazolyl wherein each 5- or 6- member heteroaromatic ring may be optionally substituted with 1-5 R20; R22 is independently: H; halogen; cyano; nitro; C^Cg alkyl; C.|-Cg haloalkyl; phenyl or benzyl optionally substituted with 1-3 R20; C.|-Cg hydroxyalkyl; C2-C6 alkoxylalkyl; C3-C6 haloalkynyl; C2-C6 alkenyl; C2-C6 haloalkenyl; C3-C6 alkynyl; C-j-Cg alkoxy; C-j-Cg haloalkoxy; C-pCg alkylthio; C-pCg alkylamino; C2-C8 dialkylamino; C3-C6 cycloalkylamino; C4-C6 (alkyl)cycloalkylamino; C2-C6 alkylcarbonyl; C2-C6 alkoxycarbonyl; C2-C6 alkylaminocarbonyl; C3-C8 dialkylaminocarbonyl; C3-C6 trialkylsilyl; ring-fused heteroaromatic rings selected from the group consisting of benzothiophenyl, quinolinyl, isoquinolinyl, thieno[2,3-b]pyridyl, 1 -methyl-1 H-thieno[2,3-c]pyrazolyl, and benzoimidazolyl, wherein each of the rings may be further substituted with 1-3 R20 ; or a 5- or 6- membered heteroaromatic ring selected from the group consisting of furanyl, pyridinyl, pyridinyl-N-oxide, pyrimidinyl, pyridazinyl, pyrazinyl, thiazolyl, triazinyl, thiadiazolyl, oxazolyl, isoxazolyl, triazolyl and thienyl; R23 is: H; halogen; C-l“Cg alkyl; C.|-Cg haloalkyl; C2-C6 dialkylamino; phenyl optionally substituted with 1-5 R20; ring-fused heteroaromatic rings selected from the group consisting of benzothiophenyl, quinolinyl, isoquinolinyl, thieno[2,3-b]pyridyl, 1-methyl-1H-thieno[2,3-c]pyrazolyl, benzofuranyl and benzoimidazolyl, 2,3-dihydro-benzofuran-2-yl, 4-methyl-4H-thieno[3,2-b]pyrrol-5-yl, 1-methyl-1 H-indol-5-yl, im-idazo[1,2-a]pyridin-2-yl, imidazo[2,1-b]thiazol-6-yl, benzothiazol-2-yl, benzo[b]thiophen-7-yl, and 1-methyl-1 H-inda-zol-3-yl, wherein each of the rings may be further substituted with 1-3 R20; naphthyl; benzo[1,3]dioxolyl; pyrrolidinonyl; oxetanyl; C.|-Cg alkylthio optionally substituted with 1-5 R20; a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11; or a 5- or 6- membered heteroaromatic ring selected from the group consisting of furanyl, pyridinyl, pyridinyl-N-oxide, pyrimidinyl, pyudazinyl, pyrazinyl, pyrazolyl, thiazolyl, triazinyl, thiadiazolyl, oxazolyl, isoxazolyl, triazolyl, imidazolyl, thiophene-2-yl and thiophen-3-yl wherein each heteroaromatic ring may be optionally substituted with 1-3 R20; R24 is H, C^Cg alkyl, C^Cg alkoxy, benzyl, or phenyl wherein each of the benzyl or phenyl may be optionally substituted with 1-3 R20; R25 is H, Ci-Cg alkyl, phenyl or benzyl optionally substituted with 1-3 R20; R26 is: H; C^Cg alkyl; C^Cg alkoxy; phenyl optionally substituted with 1-3 R20; or a 5- or 6 membered heteroaromatic ring selected from the group consisting of furanyl, pyridinyl, pyridinyl-N-oxide, pyrimidinyl, pylidazinyl, pyrazinyl, thiazolyl, triazinyl, thiadiazolyl, oxazolyl, triazolyl and isoxazolyl; R27 and R28 are independently: H;
CrC6 alkyl; benzyl or phenyl wherein each of the benzyl or phenyl may be optionally substituted with 1-3 R20;or a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11; R29 is: H; C-pCg alkyl: C-pCg haloalkyl; C-pCg alkoxyalkyl; C2-C6 alkylcarbonyl; benzyl or phenyl wherein each of the benzyl or phenyl may be optionally substituted with 1-3 R20 ; or a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11; R30 is independently halogen, cyano, nitro, C^Cg alkyl, C.|-Cg haloalkyl, C-pCg hydroxyalkyl, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, hydroxyl, C^Cg alkoxy, C^Cg haloalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 haloalkynyloxy, CrC6 alkylthio, C-j-Cg alkylsulfonyl, CrC6 haloalkylsulfonyl, C2-C6 alkenylthio, C2-C6 haloalkenylthio, C2-C6 haloalkenylsulfonyl, C3-C6 alky-nylthio, C3-C6 alkynylsulfonyl, C3-C6 haloalkynylsulfonyl, C-j-Cg alkylamino, C2-C8 dialkylamino, C3-C8 dialkylaminoc-arbonyl, C3-C6 trialkylsilyl, thiazolyl, phenyl, pyrimidinyl, or pyridyl, wherein the thiazolyl, phenyl, pyridyl, or pyrimidinyl may be optionally substituted with 1-3 R20; R31 is independently halogen, cyano, nitro, C^Cg alkyl, C-pCg haloalkyl, C-pCg hydroxyalkyl, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, hydroxyl, C1-C6 alkoxy, C-pCg haloalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 haloalkynyloxy, CrC6 alkylthio, C-pCg alkylsulfonyl, C.|-Cg haloalkylsulfonyl, C2-C6 alkenylthio, C2-C6 haloalkenylthio, C2-C6 haloalkenylsulfonyl, C3-C6 alky-nylthio, C3-C6 alkynylsulfonyl, C3-C6 haloalkynylsulfonyl, CrCg alkylamino, C2-C8 dialkylamino, C3-C8 dialkylaminoc-arbonyl, or C3-C6 trialkylsilyl; R32 is independently:
Ci-C6 alkyl, Ci-C6 haloalkyl, C.|-C6 hydroxyalkyl, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, hydroxyl, CrC6 alkoxy, C-j-Cg haloalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 haloalkynyloxy, CrC6 alkylthio, C-j-Cg alkylsulfonyl, C1-C6 haloalkylsulfonyl, C2-C6 alkenylthio, C2-C6 haloalkenylthio, C2-C6 haloalkenylsulfonyl, C3-C6 alkynylthio, C3-C6 alkynylsulfonyl, C3-C6 haloalkynylsulfonyl, C^Cg alkylamino, C2-C8 dialkylamino, C3-C8 dialkylaminocarbonyl, C3-C6 trialkylsilyl; phenyl wherein the phenyl ring may be optionally substituted with 1-3 R20 ; or a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11; R33 is independently:
CrC6 alkyl, C.|-C6 haloalkyl, phenyl or thienyl optionally substituted with 1-3 R20 ; or a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11; R34 is:
CrCg alkyl, C-j-Cg haloalkyl, C2-C6 alkoxyalkyl, CrC6 alkylamino; or a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11; R35 is: 0Γ06 alkyl, C2-C6 alkylcarbonyl; or a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11; R36 is H, cyano, C-pCg alkyl, C^Cg alkoxy, benzyl, or phenyl wherein each of the benzyl or phenyl may be optionally substituted with 1-3 R20; alternatively R32 and R36 may be taken together to form: a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11; and R37 is independently: H, halogen, or phenyl optionally substituted with 1-5 R20; C-j-Cg alkyl, CrCg haloalkyl, hydroxyl, C^Cg alkoxy, or C-j-Cg haloalkoxy; or a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11.
[0013] Another embodiment of the present disclosure may include a fungicidal composition for the control or prevention of fungal attack comprising the compounds according to the claims and a phytologically acceptable carrier material.
[0014] Yet another embodiment of the present disclosure may include a method for the control or prevention of fungal attack on a plant, the method including the steps of applying a fungicidally effective amount of one or more of the compounds according to the claims to at least one of the fungus, the plant, an area adjacent to the plant, and the seed adapted to produce the plant.
[0015] The term "alkyl" refers to a unbranched, branched, or cyclic carbon chain, including methyl, ethyl, propyl, butyl, isopropyl, isobutyl, tertiary butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like.
[0016] The term "alkenyl" refers to a branched, unbranched or cyclic carbon chain containing one or more double bonds including ethenyl, propenyl, butenyl, isopropenyl, isobutenyl, cyclohexenyl, and the like.
[0017] The term "alkynyl" refers to refers to a branched or unbranched carbon chain containing one or more triple bonds including propynyl, butynyl and the like.
[0018] As used throughout this specification, the term ’R’ refers to the group consisting of C2.g alkyl, C3_8 alkenyl or C3_8 alkynyl, unless stated otherwise.
[0019] The term "alkoxy" refers to an -OR substituent.
[0020] The term "alkoxycarbonyl" refers to a -C(0)-OR substituent.
[0021] The term "alkylcarbonyl" refers to a -C(0)-R substituent.
[0022] The term "alkylsulfonyl" refers to an -S02-R substituent.
[0023] The term "haloalkylsulfonyl" refers to a sulfonyl substitution on an alkyl which is partially substituted with halogen atoms.
[0024] The term "alkylthio" refers to an -S-R substituent.
[0025] The term "alkylaminocarbonyl" refers to a -C(0)-N(H)-R substituent.
[0026] The term "dialkylaminocarbonyl" refers to a -C(0)-NR2 substituent.
[0027] The term "alkylcycloalkylamino" refers to a cycloalkylamino substituent that is substituted with an alkyl group.
[0028] The term "trialkylsilyl" refers to -SiR3.
[0029] The term "cyano" refers to a -C^N substituent.
[0030] The term "hydroxyl" refers to a -OH substituent [0031] The term "amino" refers to a -NH2 substituent [0032] The term "alkylamino" refers to a -N(H)-R substituent [0033] The term "dialkylamino" refers to a -NR2 substituent [0034] The term "alkoxyalkoxy" refers to -0(CH2)n0(CH2)n where n is an intergerfrom 1-3 [0035] The term "alkoxyalkyl" refers to an alkoxy substitution on an alkyl.
[0036] The term "haloalkoxyalkyl" refers to an alkoxy substitution on an alkyl which may be partially substituted with halogen atoms [0037] The term "hydroxyalkyl" refers to an alkyl which is substituted with a hydroxyl group.
[0038] The term "haloalkoxy" refers to a -OR-X substituent, wherein X is Cl, F, Br, or I, or any combination thereof.
[0039] The term "haloalkyl" refers to an alkyl, which is substituted with Cl, F, I, or Br or any combination thereof.
[0040] The term "haloalkenyl" refers to an alkenyl, which is substituted with Cl, F, I, or Br or any combination thereof.
[0041] The term "haloalkynyl" refers to an alkynyl which is substituted with Cl, F, I, or Br or any combination thereof.
[0042] The term "halogen" or "halo" refers to one or more halogen atoms, defined as F, Cl, Br, and I.
[0043] The term "hydroxycarbonyl" refers to a -C(0)-OH substituent.
[0044] The term "nitro" refers to a -N02 substituent.
[0045] The term "thienyl" refers to a 5-member aromatic ring with one sulfur atom.
[0046] Throughout the disclosure, reference to the compounds of Formula I is read as also including optical isomers and salts of Formula I, and hydrates thereof. Specifically, when Formula I contains a branched chain alkyl group, it is understood that such compounds include optical isomers and racemates thereof. Exemplary salts include: hydrochloride, hydrobromide, hydroiodide, and the like.
[0047] It is also disclosed that additional substitution is allowable, unless otherwise.noted, as long as the rules of chemical bonding and strain energy are satisfied and the product still exhibits fungicidal activity.
[0048] Another embodiment of the present disclosure is a use of a compound of Formula I, as defined in claim 13, for protection of a plant againstattack by a phytopathogenic organism orthe treatment of a plant infested byaphytopatllogenic organism, comprising the application of a compound of Formula I as defined in the claims, or a composition comprising the compound to soil, a plant, a part of a plant, foliage, and/or seeds.
[0049] Additionally, another embodiment of the present disclosure is a composition useful for protecting a plant against attack by a phytopathogenic organism and/or treatment of a plant infested by a phytopathogenic organism comprising a compound of Formula I as defined in the claims and a phytologically acceptable carrier material.
Detailed Description of the Present Disclosure [0050] The compounds of the present disclosure may be applied by any of a variety of known techniques, either as the compounds or as formulations comprising the compounds. For example, the compounds may be applied to the roots, seeds or foliage of plants for the control of various fungi, without damaging the commercial value of the plants. The materials may be applied in the form of any of the generally used formulation types, for example, as solutions, dusts, wettable powders, flowable concentrates, or emulsifiable concentrates.
[0051] Preferably, the compounds of the present disclosure are applied in the fom of a formulation, comprising one or more of the compounds of Formula I according to the claims with a phytologically acceptable carrier. Concentrated formulations may be dispersed in water, or other liquids, for application, or formulations may be dust-like or granular, which may then be applied without further treatment. The formulations can be prepared according to procedures that are conventional in the agricultural chemical art.
[0052] The present disclosure contemplates all vehicles by which one or more of the compounds may be formulated for delivery and use as a fungicide. Typically, formulations are applied as aqueous suspensions or emulsions. Such suspensions or emulsions may be produced from water-soluble, water suspendable, or emulsifiable formulations which are solids, usually known as wettable powders; or liquids, usually known as emulsifiable concentrates, aqueous suspensions, or suspension concentrates. As will be readily appreciated, any material to which these compounds may be added may be used, provided it yields the desired utility without significant interference with the activity of these compounds as antifungal agents.
[0053] Wettable powders, which may be compacted to form water dispersible granules, comprise an intimate mixture of one or more of the compounds of Formula I, an inert carrier and surfactants. The concentration of the compound in the wettable powder may be from about 10 percent to about 90 percent by weight based on the total weight of the wettable powder, more preferably about 25 weight percent to about 75 weight percent. In the preparation of wettable powder formulations, the compounds may be compounded with any finely divided solid, such as prophyllite, talc, chalk, gypsum, Fuller’s earth, bentonite, attapulgite, starch, casein, gluten, montmoullonite clays, diatomaceous earths, purified silicates orthe like. In such operations, the finely divided carrier and surfactants are typically blended with thecompound(s) and milled.
[0054] Emulsifiable concentrates of the compounds of Formula I may comprise a convenient concentration, such as from about 10 weight percent to about 50 weight percent of the compound, in a suitable liquid, based on the total weight of the concentrate. The compounds may be dissolved in an inert carrier, which is either a water miscible solvent or a mixture of water-immiscible organic solvents, and emulsifiers. The concentrates may be diluted with water and oil to form spray mixtures in the form of oil-in-water emulsions. Useful organic solvents include aromatics, especially the high-boiling naphthalenic and olefinic portions of petroleum such as heavy aromatic naphtha. Other organic solvents may also be used, for example, terpenic solvents, including rosin derivatives, aliphatic ketones, such as cyclohexanone, and complex alcohols, such as 2-ethoxyethanol.
[0055] Emulsifiers which may be advantageously employed herein may be readily determined by those skilled in the art and include various nonionic, anionic, cationic and amphoteric emulsifiers, or a blend of two or more emulsifiers. Examples of nonionic emulsifiers useful in preparing the emulsifiable concentrates include the polyalkylene glycol ethers and condensation products of alkyl and aryl phenols, aliphatic alcohols, aliphatic amines or fatty acids with ethylene oxide, propylene oxides such as the ethoxylated alkyl phenols and carboxylic esters solubilized with the polyol or poly-oxyalkylene. Cationic emulsifiers include quaternary ammonium compounds and fatty amine salts. Anionic emulsifiers include the oil-soluble salts (e.g., calcium) of alkylaryl sulphonic acids, oil soluble salts orsulfated polyglycol ethers and appropriate salts of phosphated polyglycol ether.
[0056] Representative organic liquids which may be employed in preparing the emulsifiable concentrates of the compounds of the present invention are the aromatic liquids such as xylene, propyl benzene fractions; or mixed naphthalene fractions, mineral oils, substituted aromatic organic liquids such as dioctyl phthalate; kerosene; dialkyl amides of various fatty acids, particularly the dimethyl amides of fatty glycols and glycol derivatives such as the n-butyl ether, ethyl ether or methyl ether of diethylene glycol, and the methyl ether of Methylene glycol and the like. Mixtures of two or more organic liquids may also be employed in the preparation of the emulsifiable concentrate. Organic liquids include xylene, and propyl benzene fractions, with xylene being most preferred in some cases. Surface-active dispersing agents are typically employed in liquid formulations and in an amount of from 0.1 to 20 percent by weight based on the combined weight of the dispersing agent with one or more of the compounds. The formulations can also contain other compatible additives, for example, plant growth regulators and other biologically active compounds used in agriculture, [0057] Aqueous suspensions comprise suspensions ofone or more water-insoluble compounds of Formula I, dispersed in an aqueous vehicle at a concentration in the range from about 5 to about 50 weight percent, based on the total weight of the aqueous suspension. Suspensions are prepared by finely grinding one or more of the compounds, and vigorously mixing the ground material into a vehicle comprised of water and surfactants chosen from the same types discussed above. Other components, such as inorganic salts and synthetic or natural gums, may also be added to increase the density and viscosity of the aqueous vehicle.
[0058] The compounds of Formula I can also be applied as granular formulations, which are particularly useful for applications to the soil. Granular formulations generally contain from about 0.5 to about 10 weight percent, based on the total weight of the granular formulation of the compound(s), dispersed in an inert carrier which consists entirely or in large part of coarsely divided inert material such as attapulgite, bentonite, diatomite, clay or a similar inexpensive substance. Such formulations are usually prepared by dissolving the compounds in a suitable solvent and applying it to a granular carrier which has been preformed to the appropriate particle size, in the range of from about 0.5 to about 3 mm. A suitable solvent is a solvent in which the compound is substantially or completely soluble. Such formulations may also be prepared by making a dough or paste of the carrier and the compound and solvent, and crushing and drying to obtain the desired granular particle.
[0059] Dusts containing the compounds of Formula I may be prepared by intimately mixing one or more of the compounds in powdered form with a suitable dusty agricultural carrier, such as, for example, kaolin clay, ground volcanic rock, and the like. Dusts can suitably contain from about 1 to about 10 weight percent of the compounds, based on the total weight of the dust.
[0060] The formulations may additionally contain adjuvant surfactants to enhance deposition, wetting and penetration of the compounds onto the target crop and organism. These adjuvant surfactants may optionally be employed as a component of the formulation or as a tank mix. The amount of adjuvant surfactant will typically vary from 0.01 to 1.0 percent by volume, based on a spray-volume ofwater, preferably 0.05 to 0.5 volume percent. Suitable adjuvant surfactants include, but are not limited to ethoxylated nonyl phenols, ethoxylated synthetic or natural alcohols, salts of the esters or sulphosuccinic acids, ethoxylated organosilicones, ethoxylated fatty amines and blends of surfactants with mineral or vegetable oils. The formlulations may also include oil-in-water emulsions such as those disclosed in U.S. Patent Application Serial No. 11/495,228, the disclosure of which is expressly incorporated by reference herein.
[0061] The formulations may optionally include combinations that contain other pesticidal compounds. Such additional pesticidal compounds may be fungicides, insecticides, herbicides, nematocides, miticides, arthropodicides, bactericides or combinations thereof that are compatible with the compounds of the present invention in the medium selected for application, and not antagonistic to the activity of the present compounds. Accordingly, it is disclosed that the other pesticidal compound is employed as a supplemental toxicant for the same or for a different pesticidal use. The compounds of Formula I, and the pesticidal compound in the combination can generally be present in a weight ratio of from 1:100 to 100:1.
[0062] The compounds of the present disclosure may also be combined with otherfungicides to form fungicidal mixtures and synergistic mixtures thereof. The fungicidal compounds of the present disclosure are often applied in conjunction with one or more otherfungicides to control a wider variety of undesirable diseases. When used in conjunction with other fungicide(s), the presently claimed compounds may be formulated with the other fungicide(s), tank mixed with the other fungicide(s) or applied sequentially with the other fungicide(s). Such other fungicides may include 2-(thiocyanatometh-ylthio)-benzothiazole, 2-phenylphenol, 8-hydroxyquinoline sulfate, antimycin, Ampelomyces, quisqualis, azaconazole, azoxystrobin, Bacillus subtilis, benalaxyl, benomyl, benthiavalicarb-isopropyl, benzylaminobenzene-sulfonate (BABS) salt, bicarbonates, biphenyl, bismeithiazol, bitertanol, blasticidin-S, borax, Bordeaux mixture, boscalid, bromuconazole, bupirimate, calcium polysulfide, captafol, captan, carbendazim, carboxin, carpropamid, carvone, chloroneb, chloroth-alonil, chlozolinate, Coniothyrium minitans, copper hydroxide, copper octanoate, copper oxychloride, copper sulfate, copper sulfate (tribasic), cuprous oxide, cyazofamid, cyflufenamid, cymoxanil, cyproconazole, cyprodinil, dazomet, de-bacarb, diammonium ethylenebis-(dithiocarbamate), dichlofluanid, dichlorophen, diclocymet, diclomezine, dichloran, diethofencarb, difenoconazole, difenzoquat ion, diflumetorim, dimethomorph, dimoxystrobin, diniconazole, diniconazole-M.dinobuton, dinocap, diphenylamine, dithianon, dodemorph, dodemorph acetate, dodine, dodinefree base, edifenphos, enestrobin, epoxiconazole, ethaboxam, ethoxyquin, etridiazole, famoxadone, fenamidone, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenoxanil, fenpiclonil, fenpropidin, fenpropimorph, fentin, fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, flumorph, fluopicolide, fluoroimide, fluoxastrobin, fluquinconazole, flusilazole, flusulfa-mide, flutolanil, flutriafol, folpet, formaldehyde, fosetyl, fosetyl-aluminium, fuberidazole, furalaxyl, furametpyr, guazatine, guazatine acetates, GY-81, hexachlorobenzene, hexaconazole, hymexazol, imazalil, imazalil sulfate, imibenconazole, iminoctadine, iminoctadine triacetate, iminoctadine tris(albesilate), ipconazole, iprobenfos, iprodione, iprovalicarb, iso-prothiolane, kasugamycin, kasugamycin hydrochloride hydrate, kresoxim-methyl, mancopper, mancozeb, mandiprop-amid, maneb, mepanipyrim, mepronil, mercuric chloride, mercuric oxide, mercurous chloride, metalaxyl, mefenoxam, metalaxyl-M, metam, metam-ammonium, metam-potassium, metam-sodium, metconazole, methasulfocarb, methyl iodide, methyl isothiocyanate, metiram, metominostrobin, metrafenone, mildiomycin, myclobutanil, nabam, nitrothaliso-propyl, nuarimol, octhilinone, ofurace, oleic acid (fatty acids), orysastrobin, oxadixyl, oxine-copper, oxpoconazolefuma-rate, oxycarboxin, pefurazoate, penconazole, pencycuron, pentachlorophenol, pentachlorophenyl laurate, penthiopyrad, phenylmercury acetate, phosphonic acid, phthalide, picoxystrobin, polyoxin B, polyoxins, polyoxorim, potassium bicarbonate, potassium hydroxyquinoline sulfate, probenazole, prochloraz, procymidone, propamocarb, propamocarb hydrochloride, propiconazole, propineb, proquinazid, prothioconazole, pyraclostrobin, pyrazophos, pyributicarb, pyrifenox, pyrimethanil, pyroquilon, quinoclamine, quinoxyfen, quintozene, Reynoutria sachalinensis extract, silthiofam, simeco-nazole, sodium 2-phenylphenoxide, sodium bicarbonate, sodium pentachlorophenoxide, spiroxamine, sulfur, SYP-Z071, SYP-048, tar oils, tebuconazole, tecnazene, tetraconazole, thiabendazole, thifluzamide, thiophanate-methyl, thiram, tiadinil, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triazoxide, tricyclazole, tridemorph, trifloxystrobin, triflumi-zole, triforine, triticonazole, validamycin, vinclozolin, zineb, ziram, zoxamide, Candida oleophila, Fusarium oxysporum, Gliocladium spp., Phlebiopsis gigantean, Streptomyces griseoviridis, Trichoderma spp., (RS)-N-(3,5-dichlorophenyl)- 2- (methoxymethyl)-succinimide, 1,2-dichloropropane, 1,3-dichloro-1,1,3,3-tetrafluoroacetone hydrate, 1-chloro-2,4-din-itronaphthalene, 1-chloro-2-nitropropane, 2-(2-heptadecyl-2-imidazolin-1-yl)ethanol, 2,3-dihydro-5-phenyl-1,4-dithi-ine 1,1,4,4-tetraoxide, 2-methoxyethylmercury acetate, 2-methoxyethylmercury chloride, 2-methoxyethylmercury silicate, 3- (4-chlorophenyl)-5-methylrhodanine, 4-(2-nitroprop-1-enyl)phenyl thiocyanateme: ampropylfos, anilazine, azithiram, barium polysulfide, Bayer 32394, benodanil, benquinox, bentaluron, benzamacril; benzamacril-isobutyl, benzamorf, binapacryl, bis(methylmercury) sulfate, bis(tributyltin) oxide, buthiobate, cadmium calcium copper zinc chromate sulfate, carbamorph, CECA, chlobenthiazone, chloraniformethan, chlorfenazole, chlorquinox, climbazole, copper bis(3-phenyl-salicylate), copper zinc chromate, cufraneb, cupric hydrazinium sulfate, cuprobam, cyclafuramid, cypendazole, cypro-furam, decafentin, dichlone, dichlozoline, diclobutrazol, dimethirimol, dinocton, dinosulfon, dinoterbon, dipyrithione, di-talimfos, dodicin, drazoxolon, EBP, ESBP, etaconazole, etem, ethirim.fenaminosulf, fenapanil,fenitropan,fluotrimazole, furcarbanil, furconazole, furconazole-cis, furmecyclox, furophanate, glyodine, griseofulvin, halacrinate, Hercules 3944, hexylthiofos, ICIA0858, isopamphos, isovaledione, mebenil, mecarbinzid , metazoxolon, methfuroxam, methylmercury dicyandiamide, metsulfovax, milneb, mucochloric anhydride, myclozolin, N-3,5-dichlorophenyl-succinimide, N-3-nitro-phenylitaconimide, natamycin, N-ethylmercurio-4-toluenesulfonanilide, nickel bis(dimethyldithiocarbamate), OCH, phenylmercury dimethyldithio-carbamate, phenylmercury nitrate, phosdiphen, prothiocarb; prothiocarb hydrochloride, py-racarbolid, pyridinitril, pyroxychlor, pyroxyfur, quinacetol; quinacetol sulfate, quinazamid, quinconazole, rabenzazole, salicylanilide, SSF-109, sultropen, tecoram, thiadifluor, thicyofen, thiochlorfenphim, thiophanate, thioquinox, tioxymid, triamiphos, triarimol, triazbutil, trichlamide, urbacid, XRD-563, and zarilamid, IK-1140, NC-224, and any combinations thereof.
[0063] Additionally, the compounds of the present invention may be combined with other pesticides, including insecticides, nematocides, miticides, arthropodicides, bactericides or combinations thereof that are compatible with the compounds of the present invention in the medium selected for application, and not antagonistic to the activity of the present compounds to form pesticidal mixtures and synergistic mixtures thereof. The fungicidal compounds of the present disclosure may be applied in conjunction with one or more other pesticides to control a wider variety of undesirable pests. When used in conjunction with other pesticides, the presently claimed compounds may be formulated with the other pesticide(s), tank mixed with the other pesticide(s) or applied sequentially with the other pesticide(s). Typical insecticides include, but are not limited to: antibiotic insecticides such as allosamidin and thuringiensin; macrocyclic lactone insec ticides such as spinosad; avermectin insecticides such as abamectin, doramectin, emamectin, eprinomectin, ivermectin and selamectin; milbemycin insecticides such as lepimectin, milbemectin, milbemycin oxime and moxidectin; arsenical insecticides such as calcium arsenate, copper acetoarsenite, copper arsenate, lead arsenate, potassium arsenite and sodium arsenite; botanical insecticides such asanabasine, azadirachtin, d-limonene, nicotine, pyrethrins, cinerins, cinerin I, cinerin II, jasmolin IJasmolin II, pyrethrin I, pyrethrin II, quassia, rotenone, ryania and sabadilla; carbamate insecticides such as bendiocarb and carbaryl; benzofuranyl methylcarbamate insecticides such as benfuracarb, carbofuran, carbo-sulfan, decarbofuran and furathiocarb; dimethylcarbamate insecticides dimitan, dimetilan, hyquincarb and pirimicarb; oxime carbamate insecticides such as alanycarb, aldicarb, aldoxycarb, butocarboxim, butoxycarboxim, methomyl, nitri-lacarb, oxamyl, tazimcarb, thiocarboxime, thiodicarb and thiofanox; phenyl methylcarbamate insecticides such as allyx-ycarb, aminocarb, bufencarb, butacarb, carbanolate, cloethocarb, dicresyl, dioxacarb, EMPC, ethiofencarb, fenethacarb, fenobucarb, isoprocarb, methiocarb, metolcarb, mexacarbate, promacyl, promecarb, propoxur, trimethacarb, XMC and xylylcarb; dinitrophenol insecticides such as dinex, dinoprop, dinosam and DNOC; fluorine insecticides such as barium hexafluorosilicate, cryolite, sodium fluoride, sodium hexafluorosilicate and sulfluramid; formamidine insecticides such as amitraz, chlordimeform, formetanate and formparanate; fumigant insecticides such as acrylonitrile, carbon disulfide, carbon tetrachloride, chloroform, chloropicrin, para-dichlorobenzene, 1,2-dichloropropane, ethyl formate, ethylene dibromide, ethylene dichloride, ethylene oxide, hydrogen cyanide, iodomethane, methyl bromide, methylchloroform, methylene chloride, naphthalene, phosphine, sulfuryl fluoride and tetrachloroethane; inorganic insecticides such as borax, calcium polysulfide, copper oleate, mercurous chloride, potassium thiocyanate and sodium thiocyanate; chitin synthesis inhibitors such as bistrifluron, buprofezin, chlorfluazuron, cyromazine, diflubenzuron, flucycloxuron, flufenoxuron, hex-aflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron and triflumuron; juvenile hormone mimics such as epofenonane, fenoxycarb, hydroprene, kinoprene, methoprene, pyriproxyfen and triprene; juvenile hormones such as juvenile hormone I, juvenile hormone II and juvenile hormone III; moulting hormone agonists such as chromafenozide, halofenozide, methoxyfenozide and tebufenozide; moulting hormones such as α-ecdysone and ecdysterone; moulting inhibitors such as diofenolan; precocenessuch as precocene I, precocene II and precocene III; unclassified insect growth regulators such as dicyclanil; nereistoxin analogue insecticides such as bensultap, cartap, thiocyclam and thiosultap; nicotinoid insecticides such asflonicamid; nitroguanidine insecticides such as clothianidin, dinotefuran, imidacloprid and thiamethoxam; nitromethylene insecticides such as nitenpyram and nithiazine; pyridylmethyl-amine insecticides such as acetamiprid, imidacloprid, nitenpyram and thiacloprid; organochlorine insecticides such as bromo-DDT, camphechlor, DDT, pp’-DDT, ethyl-DDD, HCH, gamma-HCH, lindane, methoxychlor, pentachlorophenol and TDE; cyclodiene insecticides such as aldrin, bromocyclen, chlorbicyclen, chlordane, chlordecone, dieldrin, dilor, endosulfan, endrin, HEOD, heptachlor, HHDN, isobenzan, isodrin, kelevan and mirex; organophosphate insecticides such as bromfenvinfos, chlo-rfenvinphos, crotoxyphos, dichlorvos, dicrotophos, dimethylvinphos, fospirate, heptenophos, methocrotophos, mevin-phos, monocrotophos, naled, naftalofos, phosphamidon, propaphos, TEPP and tetrachlominphos; organothiophosphate insecticides such as dioxabenzofos, fosmethilan and phenthoate; aliphatic organothiophosphate insecticides such as acethion, amiton, cadusafos, chlorethoxyfos, chlormephos, demephion, demephion-O, demephion-S, demeton, deme-ton-O, demeton-S, demeton-methyl, demeton-O-methyl, demeton-S-methyl, demeton-S-methylsulphon, disulfoton, ethion, ethoprophos, IPSP, isothioate, malathion, methacrifos, oxydemeton-methyl, oxydeprofos, oxydisulfoton, phorate, sulfotep, terbufos and thiometon; aliphatic amide organothiophosphate insecticides such as amidithion, cyanthoate, dimethoate, ethoate-methyl, formothion, mecarbam, omethoate, prothoate, sophamide and vamidothion; oxime organothiophosphate insecticides such as chlorphoxim, phoxim and phoxim-methyl; heterocyclic organothiophosphate insecticides such as azamethiphos, coumaphos, coumithoate, dioxathion, endothion, menazon, morphothion, phosalone, pyraclofos, pyridaphenthion and quinothion; benzothiopyran organothiophosphate insecticides such as dithicrofos and thicrofos; benzotriazine organothiophosphate insecticides such as azinphos-ethyl and azinphos-methyl; isoindole organothiophosphate insecticides such as dialifos and phosmet; isoxazole organothiophosphate insecticides such as isox-athion and zolaprofos; pyrazolopyrimidine organothiophosphate insecticides such as chlorprazophos and pyrazophos; pyridine organothiophosphate insecticides such as chlorpyrifos and chlorpyrifos-methyl; pyrimidine organothiophosphate insecticides such as butathiofos, diazinon, etrimfos, lirimfos, pirimiphos-ethyl, pirimiphos-methyl, primidophos, pyrimitate and tebupirimfos; quinoxaline organothiophosphate insecticides such as quinalphos and quinalphos-methyl; thiadiazole organothiophosphate insecticides such as athidathion, lythidathion, methidathion and prothidathion; triazole organothiophosphate insecticides such as isazofos and triazophos; phenyl organothiophosphate insecticides such as azothoate, bromophos, bromophos-ethyl, carbophenothion, chlorthiophos, cyanophos, cythioate, dicapthon, dichlofenthion, eta-phos, famphur, fenchlorphos, fenitrothion fensulfothion, fenthion, fenthion-ethyl, heterophos, jodfenphos, mesulfenfos, parathion, parathion-methyl, phenkapton, phosnichlor, profenofos, prothiofos, sulprofos, temephos, trichlormetaphos-3 and trifenofos; phosphonate insecticides such as butonate and trichlorfon; phosphonothioate insecticides such as mecar-phon; phenyl ethylphosphonothioate insecticides such as fonofos and trichloronat; phenyl phenylphosphonothioate insecticides such as cyanofenphos, EPN and leptophos; phosphoramidate insecticides such as crufomate, fenamiphos, fosthietan, mephosfolan, phosfolan and pirimetaphos; phosphoramidothioate insecticides such as acephate, isocarbo-phos, isofenphos, methamidophos and propetamphos; phosphorodiamide insecticides such as dimefox, mazidox, mi- pafox and schradan; oxadiazine insecticides such as indoxacarb; phthalimide insecticides such as dialifos, phosmet and tetramethrin; pyrazole insecticides such as acetoprole, ethiprole, fipronil, pyrafluprole, pyriproie, tebufenpyrad, tolfen-pyrad and vaniliprole; pyrethroid ester insecticides such as acrinathrin, allethrin, bioallethrin, barthrin, bifenthrin, bioeth-anomethrin, cyclethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, Cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin, deltame-thrin, dimefluthrin, dimethrin, empenthrin, fenfluthrin.fenpirithrin, fenpropathrin.fenvalerate, esfenvalerate, flucythrinate, fluvalinate, tau-fluvalinate, furethrin, imiprothrin, metofluthrin, permethrin, biopermethrin, transpermethrin, phenothrin, prallethrin, profluthrin, pyresmethrin, resmethrin, bioresmethrin, cismethrin, tefluthrin, terallethrin, tetramethrin, tralom-ethrin and transfluthrin; pyrethroid ether insecticides such as etofenprox, flufenprox, halfenprox, protrifenbute and si-lafluofen; pyrimidinamine insecticides such as flufenerim and pyrimidifen; pyrrole insecticides such as chlorfenapyr; tetronic acid insecticides such as spiromesifen; thiourea insecticides such as diafenthiuron; urea insecticides such as flucofuron and sulcofuron; and unclassified insecticides such as closantel, crotamiton, EXD, fenazaflor, fenoxacrim, flubendiamide, hydramethylnon, isoprothiolane, malonoben, metaflumizone, metoxadiazone, nifluridide, pyridaben, py-ridalyl, rafoxanide, triarathene and triazamate, and any combinations thereof.
[0064] Additionally, the compounds of the present invention may be combined with herbicides that are compatible with the compounds of the present invention in the medium selected for application, and not antagonistic to the activity of the present compounds to form pesticidal mixtures and synergistic mixtures thereof. The fungicidal compounds of the present disclosure may be applied in conjunction with one or more herbicides to control a wide variety of undesirable plants. When used in conjunction with herbicides, the presently claimed compounds may be formulated with the herbicide^), tank mixed with the herbicide(s) or applied sequentially with the herbicide(s). Typical herbicides include, but are not limited to: amide herbicides such as allidochlor, beflubutamid, benzadox, benzipram, bromobutide, cafenstrole, CDEA, chlorthiamid, cyprazole, dimethenamid,dimethenamid-P,diphenamid,epronaz, etnipromid, fentrazamide.flupox-am, fomesafen, halosafen, isocarbamid, isoxaben, napropamide, naptalam, pethoxamid, propyzamide, quinonamid and tebutam; anilide herbicides such as chloranocryl, cisanilide, clomeprop, cypromid, diflufenican, etobenzanid, fenasulam, flufenacet, flufenican, mefenacet, mefluidide, metamifop, monalide, naproanilide, pentanochlor, picolinafen and propanil; arylalanine herbicides such as benzoylprop, flamprop and flamprop-M; chloroacetanilide herbicides such as acetochlor, alachlor, butachlor, butenachlor, delachlor, diethatyl, dimethachlor, metazachlor, metolachlor, S-metolachlor, pretilachlor, propachlor, propisochlor, prynachlor, terbuchlor, thenylchlor and xylachlor; sulfonanilide herbicides such as benzofluor, perfluidone, pyrimisulfan and profluazol; sulfonamide herbicides such as asulam, carbasulam, fenasulam and oryzalin; antibiotic herbicides such as bilanafos; benzoic acid herbicides such as chloramben, dicamba, 2,3,6-TBA and tricamba; pyrimidinyloxybenzoic acid herbicides such as bispyribac and pyriminobac; pyrimidinylthiobenzoic acid herbicides such as pyrithiobac; phthalic acid herbicides such as chlorthal; picolinic acid herbicides such as aminopyralid, clopyralid and picloram; quinolinecarboxylic acid herbicides such as quinclorac and quinmerac; arsenical herbicides such as cacodylic acid, CMA, DSMA, hexaflurate, MAA, MAMA, MSMA, potassium arsenite and sodium arsenite; ben-zoylcyclohexanedione herbicides such as mesotrione, sulcotrione, tefuryltrione and tembotrione; benzofuranyl alkylsul-fonate herbicides such as benfuresate and ethofumesate; carbamate herbicides such as asulam, carboxazole chlorpro-carb, dichlormate, fenasulam, karbutilate and terbucarb; carbanilate herbicides such as barban, BCPC, carbasulam, carbetamide, CEPC, chlorbufam, chlorpropham, CPPC, desmedipham, phenisopham, phenmedipham, phenmedipham-ethyl, propham and swep; cyclohexene oxime herbicides such as alloxydim, butroxydim, clethodim, cloproxydim, cy-cloxydim, profoxydim, sethoxydim, tepraloxydim and tralkoxydim; cyclopropylisoxazole herbicides such as isoxachlortole and isoxaflutole; dicarboximide herbicides such as benzfendizone, cinidon-ethyl, flumezin, flumiclorac, flumioxazin and flumipropyn; dinitroaniline herbicides such as benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, isopropalin, methalpropalin, nitralin, oryzalin, pendimethalin, prodiamine, profluralin and trifluralin; dinitrophenolherbicides such as dinofenate, dinoprop, dinosam, dinoseb, dinoterb, DNOC, etinofen and medinoterb; diphenyl ether herbicides such as ethoxyfen; nitrophenyl ether herbicides such as acifluorfen, aclonifen, bifenox, chlomethoxyfen, chlornitrofen, etnipromid, fluorodifen, fluoroglycofen, fluoronitrofen, fomesafen,furyloxyfen, halosafen, lactofen.nitrofen, nitrofluorfen andoxyfluor-fen; dithiocarbamate herbicides such as dazometand metam; halogenated aliphatic herbicides such asalorac, chloropon, dalapon, flupropanate, hexachloroacetone, iodomethane, methyl bromide, monochloroacetic acid, SMA and TCA; imi-dazolinone herbicides such as imazamethabenz, imazamox, imazapic, imazapyr, imazaquin and imazethapyr; inorganic herbicides such as ammonium sulfamate, borax, calcium chlorate, copper sulfate, ferrous sulfate, potassium azide, potassium cyanate, sodium azide, sodium chlorate and sulfuric acid; nitrile herbicides such as bromobonil, bromoxynil, chloroxynil, dichlobenil, iodobonil, ioxynil and pyraclonil; organophosphorus herbicides such as amiprofos-methyl, ani-lofos, bensulide, bilanafos, butamifos, 2,4-DEP, DMPA, EBEP, fosamine, glufosinate, glyphosate and piperophos; phe-noxy herbicides such as bromofenoxim, clomeprop, 2,4-DEB, 2,4-DEP, difenopenten, disul, erbon, etnipromid, fenteracol and trifopsime; phenoxyacetic herbicides such as 4-CPA, 2,4-D, 3,4-DA, MCPA, MCPA-thioethyl and 2,4,5-T; phenoxy-butyric herbicides such as 4-CPB, 2,4-DB, 3,4-DB, MCPB and 2,4,5-TB; phenoxypropionic herbicides such as cloprop, 4-CPP, dichlorprop, dichlorprop-P, 3,4-DP, fenoprop, mecoprop and mecoprop-P; aryloxyphenoxypropionic herbicides such as chlorazifop, clodinafop, clofop, cyhalofop, diclofop, fenoxaprop, fenoxaprop-P, fenthiaprop, fluazifop, fluazifop- P, haloxyfop, haloxyfop-P, isoxapyrifop, metamifop, propaquizafop, quizalofop, quizalofop-P and trifop; phenylenedi-amine herbicides such as dinitramine and prodiamine; pyrazolylherbicides such as benzofenap, pyrazolynate, pyrasul-fotole, pyrazoxyfen, pyroxasulfone and topramezone; pyrazolylphenyl herbicides such as fluazolate and pyraflufen; pyridazine herbicides such as credazine, pyridafol and pyridate; pyridazinone herbicides such as brompyrazon, chlori-dazon,dimidazon,flufenpyr, metflurazon, norflurazon, oxapyrazon and pydanon; pyridine herbicides such asaminopyral-id, cliodinate, clopyralid, dithiopyr, fluroxypyr, haloxydine, picloram, picolinafen, pyriclor, thiazopyrand triclopyr; pyrimi-dinediamine herbicides such as iprymidam and tioclorim; quaternary ammonium herbicides such as cyperquat, dietham-quat, difenzoquat, diquat, morfamquat and paraquat; thiocarbamate herbicides such as butylate, cycloate, di-allate, EPTC, esprocarb, ethiolate, isopolinate, methiobencarb, molinate, orbencarb, pebulate, prosulfocarb, pyributicarb, sul-fallate, thiobencarb, tiocarbazil, tri-allate and vernolate; thiocarbonate herbicides such as dimexano, EXD and proxan; thiourea herbicides such as methiuron; triazine herbicides such as dipropetryn, triaziflam and trihydroxytriazine; chloro-triazine herbicides such as atrazine, chlorazine, cyanazine, cyprazine, eglinazine, ipazine, mesoprazine, procyazine, proglinazine, propazine, sebuthylazine, simazine, terbuthylazine and trietazine; methoxytriazine herbicides such as atraton, methometon, prometon, secbumeton, simeton and terbumeton; methylthiotriazine herbicides such as ametryn, aziprotryne, cyanatryn, desmetryn, dimethametryn, methoprotryne, prometryn, simetryn and terbutryn; triazinone herbicides such as ametridione, amibuzin, hexazinone, isomethiozin, metamitron and metribuzin; triazole herbicides such as amitrole, cafenstrole, epronaz and flupoxam; triazolone herbicides such as amicarbazone, bencarbazone, carfentra-zone, flucarbazone, propoxycarbazone, sulfentrazone and thiencarbazone-methyl; triazolopyrimidine herbicides such as cloransulam, diclosulam, florasulam, flumetsulam, metosulam, penoxsulam and pyroxsulam; uracil herbicides such as butafenacil, bromacil, flupropacil, isocil, lenacil and terbacil; 3-phenyiuraciis\ urea herbicides such as benzthiazuron, cumyluron, cycluron, dichloralurea, diflufenzopyr, isonoruron, isouron, methabenzthiazuron, monisouron and noruron; phenylurea herbicides such as anisuron, buturon, chlorbromuron, chloreturon, chlorotoluron, chloroxuron, daimuron, difenoxuron, dimefuron, diuron, fenuron, fluometuron, fluothiuron, isoproturon, linuron, methiuron, methyldymron, me-tobenzuron, metobromuron, metoxuron, monolinuron, monuron, neburon, parafluron, phenobenzuron, siduron, tetrafluron and thidiazuron; pyrimidinylsulfonylurea herbicides such as amidosulfuron, azimsulfuron, bensulfuron, chlo-rimuron, cyclosulfamuron, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, im-azosulfuron, mesosulfuron, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, pyrazosulfuron, rimsulfuron, sul-fometuron, sulfosulfuron and trifloxysulfuron; triazinylsulfonylurea herbicides such as chlorsulfuron, cinosulfuron, ethametsulfuron, iodosulfuron, metsulfuron, prosulfuron, thifensulfuron, triasulfuron, tribenuron, triflusulfuron and trito-sulfuron; thiadiazolylurea herbicides such as buthiuron, ethidimuron, tebuthiuron, thiazafluron and thidiazuron; and unclassified herbicides such as acrolein, allyl alcohol, azafenidin, benazolin, bentazone, benzobicyclon, buthidazole, calcium cyanamide, cambendichlor, chlorfenac, chlorfenprop, chlorflurazole, chlorflurenol, cinmethylin, clomazone, CPMF, cresol, ortho-dichlorobenzene, dimepiperate, endothal, fluoromidine, fluridone, flurochloridone, flurtamone, fluthiacet, indanofan, methazole, methyl isothiocyanate, nipyraclofen, OCH, oxadiargyl, oxadiazon, oxaziclomefone, pentachlo-rophenol, pentoxazone, phenylmercury acetate, pinoxaden, prosulfalin, pyribenzoxim, pyriftalid, quinoclamine, rhode-thanil, sulglycapin, thidiazimin, tridiphane, trimeturon, tripropindan and tritac.
[0065] Another embodiment of the present disclosure is a method for the control or prevention of fungal attack. This method comprises applying to the soil, plant, roots, foliage, seed or locus of the fungus, or to a locus in which the infestation is to be prevented (for example applying to cereal or grape plants), a fungicidal effective amount of one or more of the compounds of Formula I. The compounds are suitable for treatment of various plants at fungicidal levels, while exhibiting low phytotoxicity. The compounds may be useful both in a protectant and/or an eradicant fashion.
[0066] The compounds have been found to have significant fungicidal effect particularly for agricultural use. Many of the compounds are particularly effective for use with agricultural crops and horticultural plants.
[0067] It will be understood by those in the art that the efficacy of the compound for the foregoing fungi establishes the general utility of the compounds as fungicides.
[0068] The compounds have broad ranges of activity against fungicidal pathogens. Exemplary pathogens may include, but are not limited to, wheat leaf blotch (Septoria tritici, also known as Mycosphaerella graminicola), apple scab ( Venturia inaequaiis), and Cercospora leaf spots of sugar beets (Cercospora beticola), peanuts (Cercospora arachidicola and Cercosporidium personatum) and other crops, and black sigatoka of bananas (Mycosphaerella fujiensis). The exact amount of the active material to be applied is dependent not only on the specific active material being applied, but also on the particular action desired, the fungal species to be controlled, and the stage of growth thereof, as well as the part of the plant or other product to be contacted with the compound. Thus, all the compounds, and formulations containing the same, may not be equally effective at similar concentrations or against the same fungal species.
[0069] The compounds are effective in use with plants in a disease-inhibiting and phytologically acceptable amount. The term "disease inhibiting and phytologically acceptable amount" refers to an amount of a compound that kills or inhibits the plant disease for which control is desired, but is not significantly toxic to the plant. This amount will generally be from about 0.1 to about 1000 ppm (parts per million), with 1 to 500 ppm being preferred. The exact concentration of compound required varies with the fungal disease to be controlled, the type of formulation employed, the method of application, the particular plant species, climate conditions, and the like. A suitable application rate is typically in the range from about 0.10 to about 4 pounds/acre (about 0.01 to 0.45 grams per square meter, g/m2).
[0070] Any range or desired value given herein may be extended or altered without losing the effects sought, as is apparent to the skilled person for an understanding of the teachings herein.
[0071] The com pounds of Formula I may be made using well-known chemical procedures. Intermediates not specifically mentioned in this disclosure are either commercially available, maybe made by routes disclosed in the chemical literature, or may be readily synthesized from commercial starting materials utilizing standard procedures.
[0072] The following examples are presented to illustrate the various aspects of the compounds of the present disclosure and should not be construed as limitations to the claims.
Examples:
Preparation of 5-Fluoro-2-(4-fluorobenzvloxv)pyrmidin-4-amine (11: [0073]
[0074] To a solution of 4-fluorobenzyl alcohol (2.56 g, 20.3 mmol) in 1,4-dioxane (20 mL) was added 60% NaH (0.813 g, 20.3 mmol) in several portions over a period of 10 min. To the magnetically stirred solution was added 2-Chloro-5-fluoropyrimidin-4-amine*(2.00g, 13.6 mmol) and the mixture was stirred at room temperature until gas evolution subsided. The reaction mixture was then heated in a CEM Discover microwave reactor at 120 °C for 90 min. The cooled reaction mixture was partitioned between ethyl acetate and water, the organic phase was concentrated, and the product was purified by column chromatography (hexane / ethyl acetate gradient) to yield 5-fluoro-2-(4-fluorobenzyloxy)pyrimidin-4-amine (1.66 g, 52% yield) as a white solid: mp 129-131 °C; 1H NMR (300MHz, CDCI3) δ 7.91 (d, J = 2.6 Hz, 1H), 7.42 (m, 2H), 7.03 (m, 2H), 5.27 (s, 2H), 5.05 (br s, 2H); MS (ESI) m/z 238 (M+H)+. *4-Amino-2-chloro-5-fluoropyrimidine can be purchased commercially orcán be prepared through known literature methods. 1. Hayashi, T.; Kawakami, T. JP Patent 2005126389 2. Durr, G.J. J. Med. Chem. 1965, 8(2), 253. 2-(3-BromobenzvloxvV5-fluoropvrimidin-4-vlamine (21: [0075]
[0076] To a magnetically stirred mixture of KO‘Bu (1.0 M in ‘BuOH, 1.36 ml, 1.36 mmol) was added (3-bromophe-nyl)methanol (0.25 g, 1.36 mmol). To the resulting solution was added 2-chloro-5-fluoropyrimidine-4-ylamine (0.10 g, 0.68 mmol) and the mixture was capped and stirred at 90 °Cfor4 h. The reaction mixture was cooled to room temperature, diluted with water, and the resulting precipitate was collected by filtration. The solid was washed with water, washed with cyclohexane, and dried in the vacuum oven. A CH2CI2 solution of the compound was loaded onto Biotage SCX column and eluted with CH2CI2 followed by 2.0 M NH3 in MeOH. The solvent was evaporated under reduced pressure to give the title compound (0.100 g, 49%) as an off-white solid: mp 143-145 °C; 1H NMR (400MHz, DMSO-d6) δ 7.90 (d, J = 2.5 Hz, 1H), 7.61 (s, 1H), 7.43 (d, J= 8.0 Hz, 1H), 7.36 (d, J= 7.7 Hz, 1H), 7.22 (t, J= 7.7 Hz, 1H), 5.28 (s, 2H), 5.20 (br s, 2H); GCMS (El) m/z 297, 299 (M)+.
Preparation of 5-Fluoro-2-H-(4-fluorophenvDethoxv1pyrimidin-4-vlamine (3): [0077]
[0078] To a magnetically stirred mixture of 4-amino-2-chloro-5-fluoropylimidine (11.10 g, 75.2 mmol) in 1-(4-Fluoroph-enyl)ethanol (11.70 g, 82.8 mmol) was added a 1.0 M solution of KOfeu in TBuOH (82.8 mL, 82.8 mmol) in one portion, and the resulting tan mixture was heated to reflux and stirred for 24 h. The solvent was removed in vacuo and the resulting red-orange oil was purified by flash chromatography (Si02, 0-»10% MeOH /CH2CI2) to give 5.5 g of red-orange oil. The oil was suspended in hexanes (100 mL) and stirred for 16 h. Water (100 mL) was added to the unchanged mixture, and the biphasic system was stirred vigorously for 1 h. The resulting cream colored solid was collected by vacuum filtration, washed with warm water (55 °C, 2 x 100 mL), and dried under vacuum at 55 °C for 16 h to give 5-fluoro-2-[1-(4-fluorophenyl)ethoxy]pyrimidin-4-ylamine (3.30 g, 17.2% yield) as a white solid: mp 96-98 °C; 1H NMR (300MHz, CDCI3) δ 7.84 (d, J= 2.6 Hz, 1H), 7.42-7.38 (m, 2H), 7.03-6.97 (m, 2H), 5.99 (q,J= 6.6 Hz, 1H), 5.09 (br s, 2H), 1.61 (d, J = 6.6 Hz, 3H); MS (ESI) m/z 252 (M+H)+, m/z 250 (M-H)-.
Preparation of 1-Phenvl-ethanone-Q-(4-amino-5-fluoropvrimidin-2-vnoxime (41: [0079]
[0080] To a magnetically stirred mixture of 4-amino-2-chloro-5-fluoropyrimidine(0.10g, 0.68mmol)and acetophenone oxime (0.092 g, 0.68 mmol) in dry DMF (3 mL) in a 5 mL Biotage Iniator microwave vessel was added NaH (0.027 g of a 60 wt. % suspension, 0.68 mmol) under a N2 atmosphere. After gas evolution ceased, the resulting mixture was sealed with a Biotage Initiator microwave septa cap and heated to 100 °C in a Biotage Initiator microwave for 60 min. The contents were poured into a vial with water (5 mL) and CH2CI2 (5 mL), and neutralized with a few drops of 2N HCI. The phases were separated and the organic extract was dried over MgS04, filtered, and evaporated under a stream of nitrogen. The crude contents were purified on silica (EtOAc/hexanes gradient) and evaporation of the product fractions gave 0.057 g (34%) of 1-Phenyl-ethanone-0-(4-amino-5-fluoro-pyrimidin-2-yl)oxime as an off-white solid: mp 163-165 °C; 1H NMR (300MHz, CDCI3) δ 8.04 (d, J = 2.6 Hz , 1H), 7.75 (m, 2H), 7.42 (m, 3H), 5.25 (bs, 2H), 2.51 (s, 3H); HPLC-MS (ESI) m/z 247 (M+H)+.
Preparation of 5-Fluoro-2-(thiophen-2-vlmethoxv)-pyrimidin-4-vlamine (51: [0081]
[0082] To a mixture of 2-chloro-5-fluoropyrimidin-4-ylamine (2.00 g, 13.5 mmol) and thiophen-2-ylmethanol (1.92 g, 16.9 mmol) with a magnetic stir bar in a 20 mL Biotage Initiator microwave reaction vessel was added KOfBu (17.0 mL of 1M in fBuOH, 17.0 mmol). The resulting mixture was sealed with a Biotage Initiator microwave septa cap and heated in a Biotage Initiator microwave to 100 °C for 30 min. The heating cycle was repeated (2x) for a total reaction time of 90 min. The contents were poured into ice-water and the pH was adjusted to neutral with 2N HCI. The resulting solid was filtered and washed with water (2x) and then 20% ether/hexanes (100 mL). The remaining solid was dried overnight at 50 °C under vacuum to give 4.17 g (68%) of 5-fluoro-2-(thiophen-2-ylmethoxy)pyrimidin-4-ylamine as a pale yellow powder: mp 92-94 °C; 1H NMR(300MHz, CDCI3) δ 7.92 (d, J = 2.7Hz, 1H), 7.29 (m, 1H), 7.13 (d, J= 3.6 Hz, 1H), 6.97 (m, 1H), 5.46 (s, 2H), 5.17 (brs, 2H); MS (ESI) m/z 226 (M+H)+.
Preparation of N-r5-Fluoro-2-(thiophen-2-vlmethoxv1pvrimidin-4-vllacetamide (61 (comparison): [0083]
[0084] In a 2 dram screw cap vial, a solution of 5-fluoro-2-(thiophen-2-ylmethoxy)-pyrimidin-4-ylamine (0.10 g, 0.4 mmol) in CH2CI2 was treated with acetyl chloride (0.032 g, 0.4 mmol,) and PS-NMM (0.42 g, 0.8 mmol), a resin-bound equivalent of A/-methyl morpholine (NMM). The mixture was shaken at RT for 12 h. The reaction mixture was filtered and the solvent evaporated to yield 0.084 g (75%) of the title compound as white solid: mp 134-136 °C; 1H NMR(300MHz, CDCI3) δ 8.24 (d, J= 2.6 Hz,1 H), 7.86 (bs, 1H), 7.31 (m, 1H), 7.23 (m, 1H), 7.00 (m, 1H), 5.54 (s, 2H), 2.58 (s, 3H); MS (ESI) m/z 268 (M+H)+.
Preparation of r5-Fluoro-2-(4-fluorobenzvloxv)pvrimidin-4-vll-(4-methvlpiperazin-1-vlmethvnamine (7) (comparison): [0085]
[0086] To a magnetically stirred mixture of paraformaldehyde (0.24 g, 8 mmol) in CH2CI2 (20 mL) was added A/-meth-ylpiperazine (0.80 g, 8.0 mmol). The suspension was stirred overnight at ambient temperature on an orbital shaker, and then 5-fluoro-2-(4-fluorobenzyloxy)pyrimidin-4-ylamine (0.47 g, 2.0 mmol) was added. The resulting mixture was stirred over the weekend at RT. The solvent was evaporated and the crude residue was washed twice with 50% ether/petroleum ether and dried under a stream of N2 to give 0.21 g (30%) of [5-fluoro-2-(4-fluorobenzyloxy)pyrimidin-4-yl](4-methyl-piperazin-1-ylmethyl)amine as a beige solid: mp 125-126 °C; 1H NMR (300MHz, CDCI3) δ 7.83 (d, J = 2.3 Hz, 1H), 7.43 (m, 2H), 7.03 (t, J = 8.5 Hz, 2H), 5.40 (bs, 1H), 5.27 (s, 2H), 4.41 (d, J = 6.8 Hz, 2H), 2.63 (bs, 4H), 2.47 (bs, 4H), 2.30 (s, 3H); HPLC-MS (ESI) m/z 350 (M+H)+.
Preparation of í5-Fluoro-2-(4-fluorobenzvloxv1pvrimidin-4-vl1triethvlsilanvlamine (8) (comparison): [0087]
[0088] To a magnetically stirred mixture of 5-fluoro-2-(4-fluorobenzyloxy)pyrimidin-4-ylamine (0.25 g, 1.05 mmol) in dry THF (5 mL) at 0 °C was added NaH (0.042 g of 60 wt. % suspension in mineral oil, 1.05 mmol). When bubbling ceased, triethylsilyl chloride (0.158 g, 1.05 mmol) was added dropwise (neat) via syringe. After stirring overnight at ambient temperature, the reaction mixture was poured into ether and washed with a mixture of aqueous saturated sodium bicarbonate and brine solution. The organic layer was separated, dried over Na2S04, filtered, and evaporated to give a white solid. This crude material was purified on silica by column chromatography (EtOAc / hexanes gradient) to give 0.121 g (33%) of [5-fluoro-2-(4-fluorobenzyloxy)pyrimidin-4-yl]-triethylsilanylamine as a clear yellow oil: 1H NMR (300MHz, CDCI3) δ 7.89 (d, J= 2.5 Hz, 1H), 7.39 (m, 2H), 7.03 (t, J= 8.6 Hz, 2H), 5.27 (s, 2H), 4.53 (s, 1H), 0.99 (m, 9H), 0.83 (m, 6H); HPLC-MS (ESI) mlz 352 (M+H)+.
Preparation of r5-Fluoro-2-(4-fluorobenzvloxvlPvrimidin-4-vllfe/s-carbamic acid 4-fluorophenvl ester (9) fcomparison): [0089]
[0090] To a magnetically stirred ice-cold mixture of 5-fluoro-2-(4-fluorobenzyloxy)pyrimidin-4-ylamine (0.25 g, 1.05 mmol) in dry THF (5 mL) was added NaH (0.042 g of a 60 wt. % suspension in mineral oil, 1.05 mmol). After bubbling ceased, 4-fluorophenyl chloroformate (0.184 g, 1.05 mmol) was added dropwise as a solution in dry THF. After stirring one hour, the reaction was partitioned between EtOAc and brine solution. The organic extract was dried over Na2S04, filtered, and evaporated. The crude material was purified on silica using a gradient of EtOAc/Hex and then MeOH/EtOAc to give 0.054 g (14%) of [5-fluoro-2-(4-fluorobenzyloxy)pyrimidin-4-yl]b/s-carbamic acid 4-fluorophenyl ester as a white solid: mp 103-105 °C; 1H NMR(300MHz, CDCI3) δ 8.58 (d, J= 2.2 Hz, 1H), 7.43 (m, 2H), 7.08 (m, 10H), 5.40 (s, 2H); HPLC-MS (ESI) mlz 514 (M+H)+.
Preparation of r5-Fluoro-2-(4-fluorobenzvloxv)pvrmidin-4-vllcarbamic acid phenol ester (10) (comparison): [0091]
[0092] To a stirred mixture of 5-fluoro-2-(4-fluorobenzyloxy)pyrimidin-4-ylamine (0.20 g, 0.84 mmol) in dry THF (3 mL) at ice-bath temperatures was added NaH (0.034 g of 60 wt. % suspension in mineral oil, 0.84 mmol). When bubbling ceased, the resulting mixture was transferred (dropwise) via cannula to an ice-cold, stirred mixture of diphenyl carbonate (1.8 g, 8.4 mmol) in dry THF (5 mL). The mixture was stirred overnight, poured into EtOAc, and washed with saturated aq. NH4CI solution followed by brine solution. The EtOAc layer was separated, dried over Na2S04, filtered, and evaporated. The crude material was purified on silica gel using a gradient of EtOAc and hexanes to give 0.063 g (21%) of [5-fluoro-2-(4-fluorobenzyloxy)pyrimidin-4-yl]carbamic acid phenyl ester as a white solid: mp 129-131 °C; 1H NMR (300MHz, CDCI3) δ 8.28 (d, J = 2.3 Hz, 1H), 7.43 (m, 5H), 7.30-7.20 (m, 2H), 7.02 (t, J = 8.6 Hz, 2H), 5.38 (s, 2H); HPLC-MS (ESI) mlz 358 (M+H)+.
Preparation of N-f5-Fluoro-2-(4-fluorobenzvloxv)pvrimidin-4-vl1oxalamic acid ethyl ester (111 (comparison): [0093]
[0094] To a mixture of 5-fluoro-2-(4-fluorobenzyloxy)pyrimidin-4-ylamine (0.235 g, 0.99 mmol), N-methyl morpholine on polystyrene (0.538 g, 1.24 mmol), and CH2CI2 (5 mL) was added chloro-oxo-acetic acid ethyl ester (0.135 g, 0.99 mmol) and the resulting mixture was agitated on an orbital shaker for 16 h. The reaction contents were filtered onto an acidic SPE cartridge and eluted with CH2CI2. The CH2CI2 filtrate was evaporated to give 0.165 g (50%) of N-[5-fluoro-2-(4-fluorobenzyloxy)pyrimidin-4-yl]oxalamic acid ethyl ester as a clear oil: 1H NMR (300MHz, CDCI3) δ 9.21 (bs, 1H), 8.38 (d, J = 2.3 Hz, 1 H), 7.48 (m, 2H), 7.03 (t, J = 8.5 Hz, 2H), 5.40 (s, 2H), 4.48 (q, J = 7.1 Hz, 2H), 1.45 (t, J = 7.1 Hz, 3H); HPLC-MS (ESI) mlz 338 (M+H)+.
Preparation of 3.4-Dichloroisothiazole-5-carboxvlic acid í5-fluoro2-(4-fluorobenzvl-oxv)pvrimidin-4-vl1amide (121 fcom-parisont: [0095]
[0096] To a suspension of 3,4-dichloroisothiazole-5-carboxylic acid (0.15 g, 0.76 mmol) in oxalyl chloride (2 mL) was added a catalytic amount of dimethylformamide (2 drops) and the mixture was heated to 80 °C and stirred for 2 h. The excess oxalyl chloride was removed on the rotary evaporator. Meanwhile, 5-fluoro-2-(4-fluorobenzyloxy)-pyrimidin-4-ylamine (0.17 g, 0.68 mmol) was dissolved in THF (1 mL), treated with LiHMDS (1M in THF, 0.76 mL, 0.76 mmol) and stirred for 10 min. The freshly prepared 3,4-dichlorothiazole-5-carbonyl chloride*, dissolved in THF (1 mL), was added and the reaction was capped and stirred for 12 h. The reaction was diluted with water and the target compound was extracted with CH2CI2 (3 x 5mL). The combined extracts were dried over MgS04 and then evaporated under reduced pressure. The mixture was eluted with CH2CI2 through an anionic-exchange solid phase extraction column and then further purified by reverse-phase chromatography to give 3,4-dichloroisothiazole-5-carboxylic acid [5-fluoro-2-(4-fluor-obenzyloxy)pyrimidin-4-yl]amide (0.035 g, 12%) as a tan solid: mp 87-90 °C; 1H NMR (400 MHz, DMSO-d6) δ 11.78 (s, 1H), 8.67 (s, 1H), 7.51-7.48 (m, 2H), 7.24-7.19 (m, 2H), 5.25 (s, 2H); MS (ESI) mlz 417 (M+H)+; 415 (M-H)’.
*Nagata, T.; Kogure, A.; Yonekura, N.; Hanai, R.; Kaneko, I.; Nakano, Y. JP 2007211002 A
Preparation of r5-Fluoro-2-(4-fluorobenzvloxv')Pvrimidin-4-vl1phosphoramidic acid diethyl ester (131 (comparison): [0097]
[0098] To a magnetically stirred solution of 5-fluoro-2-(4-fluorobenzyloxy)pyrimidin-4-ylamine (0.10 g, 0.42 mmol) in dry THF (5 mL) under a nitrogen atmosphere was added NaH (0.017 g of a 60 wt.% suspension, 0.42 mmol) and the mixture was stirred until bubbling ceased. Diethyl chlorophosphate (0.073 g, 0.42 mmol) was added dropwise, and the mixture was stirred at ambient temperature for 1h. The reaction mixture was evaporated to dryness and the residue dissolved in EtOAc and washed saturated aqueous NH4CI solution. The organic layer was separated, dried over Na2S04, filtered, and evaporated. The crude material was purified on silica (acetone/CH2CI2 gradient) to give 0.017 g (11%) of [5-fluoro-2-(4-fluorobenzyloxy)pyrimidin-4-yl]phosphoramidic acid diethyl ester asawhite solid: mp 109-111 °C; 1H NMR (300MHz, CDCI3) δ 8.10 (t, J= 1.8 Hz, 1H), 7.43 (m, 2H), 7.03 (t, J = 8.5 Hz, 2H), 6.18 (brs, 1H), 5.35 (s, 2H), 4.25 (m, 4H), 1.38 (t, J = 7.1 Hz, 6H); HPLC-MS (ESI) mlz 374 (M+H)+.
Preparation of r5-Fluoro-2-(4-fluorobenzvloxv)pvrimidin-4-vl1(1-methoxypropvl)amine (14)(comparison): [0099]
[0100] To a solution of 5-fluoro-2-(4-fluorobenzyloxy)pyrimidin-4-ylamine (0.10 g, 0.42 mmol) in propionaldéhyde (2 mL) was added a catalytic amount of camphorsulfonic acid. The mixture was agitated on an orbital shaker at room temperature for 4 h and then evaporated to dryness. Methanol (2 mL) was added, and the resulting solution was warmed to 60 °C for 1 h. After evaporation, the crude product was purified by reverse phase chromatography to yield the title compound (0.030 g, 24% yield) as a clear, colorless oil: 1H NMR (300MHz, CDCI3) δ 7.91 (d, J= 2.5 Hz, 1H), 7.47-7.41 (m, 2H), 7.09-7.01 (m, 2H), 5.41 (dt, J= 9.9 and 6.0 Hz, 1H), 5.30 (s, 2H), 5.2 (bd, J~ 10 Hz, 1H), 3.12 (s, 3H), 1.88-1.60 (m, 2H), 0.98 (t, J = 7.1 Hz, 3H). HPLC-MS 308 (ES“), 310 (ES+).
Preparation of r5-Fluoro-2-(4-methvlbenzvloxv)pvrimidin-4-vlaminolmethanol (161(comparison): [0101]
[0102] To a solution of 5-fluoro-2-(4-methylbenzyloxy)pyrimidin-4-ylamine (0.10 g, 0.43 mmol) in dioxane (2 mL) was added paraformaldehyde (0.060 g, 2 mmol) and the mixture was agitated on an orbital shaker at 90 °Cfor 16 h, cooled, and evaporated to dryness. Purification by reverse phase chromatography afforded 0.070 g (63%) of the title compound as a white solid: mp 97-98°C; 1H NMR (CDCI3) δ 7.94 (d, J = 2.5Hz, 1H), 7.36 (d, J - 7.9Hz; 2H), 7.19 (d, J = 7.9Hz, 2H), 5.97 (bs, 1H), 5.33 (s, 2H), 5.04-4.99 (m, 2H), 3.39 (t, J = 8.0Hz, 1H),2.37 (s, 3H); MS (ESI) mlz 264 (M+H)+.
Preparation of Benzvloxvmethvli5-fluoro-2-(4-fluorobenzvloxv)pvrimidin-4-vllamine (181 (comparison^ [0103]
[0104] To a mixtureof[5-fluoro-2-(4-fluorobenzyloxy)pyrimidin-4-ylamino]methanol(0.10g,3.7 mmol) in benzyl alcohol (1 mL) was added a catalytic amount of p-toluene sulfonic acid. After 30 min, the reaction was cooled to room temperature and partitioned between ethyl acetate and saturated sodium bicarbonate. The phases were separated and the organic portion was dried over anhydrous Na2S04, filtered and evaporated to obtain the crude product. Purification by reverse phase chromatography afforded 0.094 g (70%) of the title compound as a white solid: mp 64-66 °C; 1H NMR (CDCI3) δ 7.93 (d, J = 2.7Hz, 1H), 7.47-7.40 (m, 2H), 7.37-7.29 (m, 5H), 7.08-7.00 (m, 2H), 5.81-5.70 (bm, 1H), 5.29 (s, 2H), 5.12 (d, J = 6.9Hz, 2H), 4.63 (s, 2H); MS (ESI) mlz 358 (M+H)+.
Preparation of 2.2-Dimethvlpropionic acidi5-fluoro-2-(4-fluorobenzvloxv’)pvrimidin-4-vlaminolmethvl ester (191 (comparison): [0105]
[0106] To a mixture of [5-fluoro-2-(4-fluorobenzyloxy)pyrimidin-4-ylamino]methanol (0.10 g, 0.37 mmol) in pyridine (2 mL) was added trimethylacetyl chloride (0.048 g, 0.40 mmol), and the mixture was agitated on an orbital shaker at 60 °C for 4 h. The reaction mixture was cooled, evaporated to dryness, and partitioned between EtOAc and water. The organic layer was dried over Na2S04, filtered, and evaporated to yield the title compound (0.078 g, 60% yield) as a white solid: mp 134-135 °C; 1H NMR(300MHz, CDCI3) δ 7.97 (d, J = 2.5 Hz, 1H), 7.49-7.44 (m,2H), 7.11-7.03 (m, 2H), 6.17 (bt, J~1 Hz, 1H), 6.17 (d, J= 7.4 Hz, 2H), 5.33 (s, 2H), 1.20 (s, 9H); HPLC-MS mlz 352 (M+H)+.
Preparation of N’-i5-Fluoro-2-(4-fluorobenzvloxv)Dvrimidin-4-vl1-N.A/ dimethvl-formamidine (20)(comparison): [0107]
[0108] To a magnetically stirred solution of 5-fluoro-2-(4-fluorobenzyloxy)pyrimidin-4-ylamine (1.00 g, 4.2 mmol) in /\/,/\/-dimethylformamide (DMF, 20 mL) was added A/,A/-dimethylformamide dimethyl acetal (0.55 g, 4.6 mmol) and stirring was continued 16 h at RT. The solution was poured into 100 mL of ice water, whereupon a white precipitate was produced. The mixture was cooled at 0 °C for 1 h and then filtered to produce the title compound (1.10 g, 89%) as a white solid: mp 113-115 °C; 1H NMR (CDCI3) δ 8.65 (s, 1H), 8.04 (d, J = 2.6 Hz, 1H), 7.46-7.40 (m, 2H), 7.07-6.98 (m, 2H), 5.30 (s, 2H), 3.17 (s, 3H), 3.16 (s, 3H); MS (ESI) mlz 292 (M+H)+. Anal. Calcd for C^H^^O: C, 57.53; H, 4.83; N, 19.17. Found: C, 57.67; H, 4.84; N, 19.09.
Preparation of r5-Fluoro-2-(4-fluorobenzvloxvlpvrimidin-4-vl1-ri-pvrrolidin-1-vl-methvlidene1amine (211 (comparison): [0109]
[0110] To a solution of N’-[5-fluoro-2-(4-fluorobenzyloxy)pyrimidin-4-yl]-N,N-dimethylformamidine (0.1 Og, 0.36 mmol) in toluene (2 mL) was added pyrrolidine (0.051 g, 0.72 mmol) and a catalytic amount of camphorsulfonic acid. The vented vial was placed on an orbital shaker, agitated at 90 °C for 16 h, cooled, and evaporated to dryness. Purification by reverse phase chromatography afforded the title compound (0.060 g, 53% yield) as a white solid: mp 102-103 °C; 1H NMR (300MHz, CDCI3) δ 8.87 (s, 1H), 8.06 (d, J = 2.7 Hz, 1H), 7.49-7.42 (m, 2H), 7.09-7.01 (m, 2H), 5.32 (s, 2H), 3.73-3.62 (m, 4H), 2.07-1.96 (m, 4H); HPLC-MS (ESI) mlz 319 (M+H)+.
Preparation of N-f5-Fluoro-2-(4-fluorobenzvloxv')pvrimidin-4-vl1-N’-hvdroxv-formamidine (22) (comparison^ [0111]
[0112] To a solution of N’-[5-fluoro-2-(4-fluorobenzyloxy)pyimidin-4-yl]-N,N-dimethyl-formamidine_(0.10g, 0.34 mmol) in EtOH (2 mL) was added hydroxylamine hydrochloride (0.047 g, 0.68 mmol) and the mixture was agitated on an orbital shaker for 1.5 h at 50 °C. The reaction mixture was cooled and evaporated to dryness. Water was added to produce a slurry which was filtered to isolate the title compound (0.090 g, 94% yield) as a white solid: mp 169-171 °C; 1H NMR (300MHz, CDCI3) δ 8.15 (d, J = 2.2 Hz, 1H), 8.02 (bs, 2H), 7.49-7.43 (m, 2H), 7.11-7.02 (m, 3H), 5.35 (s, 2H); HPLC-MS (ESI) mlz 281 (M+H)+, 279 (M-H)“.
Preparation of N-i5-Fluoro-2-(4-fluorobenzvloxv)pvrimidin-4-vl1-N’-cvanoformamidine (231 (comparison^ [0113]
[0114] Cyanamide (8.00 g, 190.0 mmol) was stirred at reflux in triethylorthoformate (60 mL) for 2 h. The reaction was cooled to room temperature and distilled to provide ethyl-N-cyanoimidate (12.5 g, bp = 110-112 °C/45 mm Hg).* To this imidate (1 mL) was added 5-fluoro-2-(4-fluorobenzyloxy)pyrimidin-4-ylamine (0.05 g, 0.2 mmol) and the mixture was heated at 90 °C for 4 h, cooled, diluted with chloroform, filtered, and evaporated. The crude product was purified by reverse phase chromatography to furnish 0.053 g (17%) of the title compound as an off white solid: mp 148-149 °C; 1H NMR (300MHz, CDCI3) δ 9.45 and 9.33 (bd, bs, J « 10 Hz, 1H), 8.33 and 8.25 (2d, J « 2Hz, 1H), 7.46-7.38 (m, 2H), 7.11-7.01 (m, 2H), 5.35 and 5.33 (2s, 2H); HPLC-MS (ESI) mlz 290 (M+H)+, 288 (M-H)-. * Bridsen, Peter K., and Wang, Xiaodong, Synthesis, 1995, 855-8.
Preparation of N’-r5-Fluoro-2-(4-fluorobenzvloxv1pvrimiidin-4-vl1-N.N-dimethvl-propionamidine (241 (comparison'): [0115]
[0116] To a solution of A/,A/-Dimethylpropionamide (0.202 g, 2.0 mmol) in CHCI3 (2 mL) was added phosphorous oxychloride (POCI3, 0.066 g, 0.43 mmol) and the mixture was agitated on an orbital shaker at room temperature for 1 h. Triethylamine (0.22 g, 2.2 mmol) and 5-fluoro-2-(4-fluorobenzyloxy)pyrimidin-4-ylamine (0.10 g, 0.40 mmol) were added, and the mixture was agitated at 50 °C for 3 h, cooled to room temperature, partitioned between chloroform and water, the phases separated, and the organics evaporated under reduced pressure. Purification by reverse phase chromatography afforded the title compound (0.042 g, 31% yield) as a yellow oil: 1H NMR (300MHz, CDCI3) δ 8.87 (s, 1H), 8.04 (d, J = 2.5 Hz, 1H), 7.46-7.40 (m, 2H), 7.07-6.99 (m, 2H), 5.30 (s, 2H), 3.13 (s, 6H), 2.55 (q, J = 7.7 Hz, 2H), 1.15 (t, J= 7.7 Hz, 3H); HPLC-MS (ESI) mlz 321 (M+H)+.
Preparation of N’-(5-Fluoro-2-hvdroxv-pvrimidin-4-vn-N.N-dimethvl-formamidine (251 (comparison): [0117]
[0118] To a magnetically stirred solution of 4-amino-5-fluoro-pyrimidin-2-ol* (4.00 g, 31.0 mmol) in DMF (100 mL) was added A/,A/-dimethylformamide dimethyl acetal (4.00 g, 34.0 mmol). The mixture was stirred at room temperature for 72 h, diluted with diethyl ether (200 mL), and filtered. The solid product was washed with heptane to give the title compound (5.23 g, 92% yield) as a white solid: mp 240-243 °C; 1H NMR (300MHz, DMSO-d6) δ 10.7 (bs, 1H), 8.59 (s, 1H), 7.7 (d, J= 5.6 Hz, 1H), 3.18 (s, 3H), 3.06 (s, 3H); HPLC-MS (ESI) mlz 185 (M+H)+, 183 (M-H)’. *4-amino-5-fluoro-pyrimidin-2-ol can be purchased commercially..
Preparation of Carbonic acid 4-fdimethvlamino-methvleneamino')-5-fluoropvrimidin-2-vl ester ethyl ester (261 ('comparison): [0119]
[0120] To a solution of N’-(5-fluoro-2-hydroxy-pyrimidin-4-yl)-N,N-dimethylformamidine (0.10,0.54 mmol) in CH2CI2 (2 mL) were added triethylamine (0.20 g, 2.0 mmol) and ethyl chloroformate (0.065 g, 0.60 mmol), and the mixture was agitated on an orbital shaker at room temperature overnight. The reaction was diluted with CH2CI2 and the solution was washed with water, dried over MgS04, filtered and evaporated. The crude product was purified by silica gel column chromatography (EtOAc / petroleum ether gradient) to yield 0.031 g (22%) of the title compound as a white solid: mp 124-126 °C; 1H NMR(300MHz, CDCI3) δ 8.67 (s, 1H), 8.19 (d, J= 2.2 Hz, 1H), 4.35 (q, J = 7.14 Hz, 2H), 3.21 (s, 6H), 1.40 (t, J = 7.14 Hz, 3H); HPLC-MS (ESI) mlz 258 (M+H)+.
Preparation of Benzoic acid 4-(dimethvlamino-methvleneamino)-5-fluoropvrimidin-2-vl ester (27) (comparison): [0121]
[0122] To a suspension of N’-(5-fluoro-2-hydroxypyrimidin-4-yl)-N,N-dimethylformamidine (0.10 g, 0.54 mmol) in pyridine (2 mL) was added benzoyl chloride (0.084 g, 0.60 mmol), and the mixture was agitated on an orbital shaker for 16 h at RT. The reaction mixture was partitioned between EtOAc and saturated aq NaHC03, and the organic phase was dried over solid MgS04, filtered, and evaporated to give the title compound (0.147 g 94%) as a white solid: mp 136-138 °C; 1H NMR (300MHz, CDCI3) δ 8.69 (s, 1H), 8.27 (d, J= 2.4Hz, 2H), 8.25-8.20 (m, 2H), 7.69-7.63 (m, 1H), 7.56-7.49 (m, 2H), 3.23 (s, 3H), 3.20 (s, 3H); HPLC-MS(ESI) mlz 289 (M+H)+.
Preparation of Benzenesulfonic acid 4-(dimethvlamino-methvleneamino')-5-fluoro-pvrimidin-2-vl ester(28Hcomparison'): [0123]
[0124] To a suspension of N’-(5-fluoro-2-hydroxypyrimidin-4-yl)-N,N-dimethylformamidine (0.10 g, 0.54 mmol) in pyridine (2 mL) was added benzene sulfonyl chloride (0.106 g, 0.60 mmol) and the mixture was agitated on an orbital shaker for 16 h at room temperature. The reaction mixture was partitioned between EtOAc and saturated aq NaHCOs, and the organic phase was dried over solid MgS04, filtered, and concentrated under reduced pressure. Purification by reverse phase chromatography (H20 / MeCN gradient) afforded the title compound (0.089 g, 46% yield) as a white solid: mp 124-125 °C; 1H NMR (300MHz, CDCI3) δ 8.54 (s, 1H), 8.12-8.07 (m, 3H), 7.73-7.66 (m, 1H), 7.62-7.56 (m, 2H), 3.21 (s, 6H); HPLC-MS (ESI) mlz 325 (M+H)+.
Preparation of Benzenesulfonic acid 4-amino-5-fluoropyrimidin-2-vl ester (29): [0125]
[0126] To a solution of HCI in doxane (3 mL of 10%) was added benzenesulfonic acid 4-(dimethylamino-methylene-amino)-5-fluoropyrimidin-2-yl ester (0.090, 0.3 mmol) and the mixture was agitated on an orbital shaker at room temperature for 1.5 h. The solvent was removed by evaporation and the residue was dissolved in a 1:1 solution of dioxane and water (2.5 mL) and treated with saturated aq NaHC03 (0.5 mL). After 16 h, the reaction mixture was partitioned between EtOAc and water and the organic phase was dried over Na2S04, filtered, and the solvent evaporated to yield the title compound (0.059 g, 79% yield) as a white solid: mp 139-141 °C; 1H NMR (300MHz, DMSO- d6) δ 8.05-8.00 (m, 3H), 7.90-7.75 (m, 3H), 7.70-7.63 (m, 2H); HPLC-MS (ESI) mlz 268 (M-H)“, 270 (M+H)+.
Preparation of Benzenesulfonic acid 4-amino-5-fluoropvrimidin-2-vl ester (291: [0127]
[0128] To a suspension of 5-fluorocytosine (0.177 g, 1.4 mmol) in pyridine (5 mL) was added and benzene sulfonyl chloride (0.284 g, 1.6 mmol) and the mixture was stirred at room temperature for 2 h. The reaction mixture was evaporated to dryness and the crude material purified by reverse phase chromatography to yield the title compound (0.106 g, 29% yield) as a white solid: mp 145-146 °C; 1H NMR (300MHz, DMSO- d6) δ 8.05-8.00 (m, 3H), 7.9-7.75 (m, 3H), 7.70-7.63 (m, 2H); HPLC-MS (ESI) mlz 270 (M+H)+, 268 (M-H)’.
Preparation of (2-Fluorobenzvl)-r5-fluoro-2-(4-fluorobenzvloxv)pvrimidin-4-vl1amine OOKcomparisonl: [0129]
A) A magnetically stirred solution of 2,4-dichloro-5-fluoropyrimidine* (0.105 g, 0.63 mmol) in 5 mL of dry THF was treated with 2-fluorobenzylamine (0.085 g, 0.68 mmol) and excess triethylamine, and the resulting mixture was heated at 80 °C for 5 h. The reaction mixture was partitioned between CH2CI2 and dilute HCI, and the organic phase was washed with brine, dried over Na2S04, and filtered. The solvent was removed under reduced pressure to yield 0.157 g (97 %) of the title compound as a yellow solid: mp 117-118 °C; 1H NMR (300MHz, CDCI3) δ 7.90 (d, J = 2.6, 1 Η), 7.47- 7.27 (m, 2H), 7.21 - 7.01 (m, 2H), 5.54 (s, 1H), 4.76 (d, J= 5.9, 2H); MS (ESI) mlz 256 (M+H)+. *2,4-Dichloro-5-fluoropyrimidine can be purchased commercially. B) A solution of (2-chloro-5-fluoropyrimidin-4-yl)-(2-fluorobenzyl)amine* (0.103 g, 0.40 mmol) in 5 mL of dry THF was treated with 4-fluorobenzylalcohol (0.062 g, 0.49 mmol) and a 1.0 M solution of KOfBu in fBuOH (0.4 mL, 0.4 mmol). The mixture was heated at 80 °C in a sealed vial for 18 h, partitioned between CH2CI2 and water, and the organic phase was washed with brine, dried over Na2S04, and filtered. The solvent was removed under reduced pressure and the residue purified by flash column chromatography (Si02, 10->20% EtOAc / petroleum ether) to yield the title compound (0.157 g, 42%) as a white solid: mp 83-84 °C; 1H NMR(300MHz, CDCI3)0 7.83 (d, J = 2.8, 1H), 7.45 - 7.27 (m, 5H), 7.15 - 6.96 (m, 5H), 5.37 (brs,1H), 5.29 (s,3H),4.74(d,J= 5.9,3H); MS (ESI) m/z346(M+H)+ ‘Singh, R.; Argade, A.; Payan, D.G.; Clough, J.; Keim, H.; Sylvain, C.; Li, H.; Bhamidipati, S., WO 2004014382 A1 20040219
Preparation of 5-fluoro-2-(3-methoxvbenzvloxv1-4-(1-(4-methoxvphenvn-hvdrazinvnpyrimidine (31 Kcomparison): [0130]
A) A 1.0 M solution of KOfBu in KOfBu (66 mL, 66 mmol) was added to a mixture of 2,4-dichloro-5-fluoropyrimidine (5.04 g, 30.1 mmol) and 3-methoxybenzyl alcohol (7.8 mL, 62.8 mmol) in a 250 mL round bottom flask. A significant exotherm was observed and the resulting mixture was stirred at room temperature for 2 h. The reaction was diluted with EtOAc (100 mL) and washed with brine (50 mL x 2). The organic layer was dried over MgS04, filtered, and concentrated under reduced pressure. Crystallization from hot EtOH provided a material which was collected on a fritted funnel and rinsed with ice-cold EtOH to provide the title compound (7.94 g, 71%) as a white solid: mp 81-83 °C; 1H NMR (300 MHz, CDCI3) δ 8.10 (d, J= 2.3 Hz, 1H), 7.29 (m, 2H), 7.02 (m, 4H), 6.87 (dt, J= 2.2, 7.8 Hz, 2H), 5.44 (s, 2H), 5.35 (s, 2H), 3.82 (s, 3H), 3.82 (s, 3H); MS (ESI) mlz 371 (M+H)+. B) A solution of 2.0 N KOH in water (85 mL, 170 mmol) was added to a mixture of 5-fluoro-2,4-bis(3-methoxyben-zyloxy)pyrimidine (7.9 g, 21.3 mmol) and EtOH (21 mL) in a 500 mL round bottom flask. A reflux condenser was attached, and the reaction was heated at 95 °C for 16 h. After cooling to room temperature, the reaction mixture was washed with Et20 (2 x 50 mL), and then acidified with 1 N HCI to pH 3. The resulting solid material was collected on a fritted funnel. Subsequent extraction with excess EtOAC, and concentration under reduced pressure provided the title compound (3.63 g, 68%) as a white solid: mp 136-139; 1H NMR (300 MHz, DMSO-d6) δ 12.97 (brs, 1H), 7.87 (d, J= 3.7 Hz, 1H), 7.30 (t, J= 7.9 Hz, 1H), 7.00 (m, 2H), 6.91 (dd, J= 1.8, 8.0 Hz, 1H), 5.29 (s, 2H), 3.74 (s, 3H); MS (ESI) m/z 251 (M+H)+. C) An oven-dried 100 mL Schlenk flask was charged with 5-fluoro-2-(3-methoxybenzyloxy)pyrimidin-4-ol (3.63 g, 14.5 mmol) and A/,/V-dimethylaniline (3.7 mL, 29.2 mL). Phosphorous oxychloride (POCI3, 40 mL, 429 mmol) was added, and resulting solution was heated to 95 °C under nitrogen. After 2 h, the reaction was cooled to room temperature and concentrated to constant volume under reduced pressure at 50 °C. The remaining residue was diluted with Et20 (50 mL) and washed with 1 N HCI (2 x 50 mL). Concentration at reduced pressure provided a solid, which was washed with water and collected by vacuum filtration. The title compound (4.09 g, 105%) was isolated as a white solid: mp 96-100 °C; 1H NMR (300 MHz, DMSO-d6) δ 8.81 (d, ,7 = 0.8 Hz, 1H), 7.30 (t, J = 8.1 Hz, 1H), 7.02 (m, 2H), 6.91 (dd, ,7 = 2.3, 8.3 Hz, 1H), 5.34 (s, 2H), 3.75 (s, 3H); MS (ESI) m/z 269 (M+H)+. D) To a mixture of 4-chloro-2-(3-methoxybenzyl)-5-fluoropyrimidine (0.153 g, 0.568 mmol) and 4-methoxyphenyl-hydrazine hydrochloride (0.324 g, 1.85 mmol) in ethanol (5 mL) was added triethylamine (0.272, 2.69 mmol) and the mixture was heated to 50 °C for 16 h. The reaction was cooled to room temperature and diluted with Et20 (50 mL). The Et20 solution was washed with water (2 x 50 mL), dried over MgS04, filtered, and concentrated. The residue was triturated with Et20 to obtain 5-fluoro-2-(3-methoxy-benzyloxy)-4-(1-(4-methoxyphenyl)hydrazinyl)py-rimidine (0.113 g, 54% yield) as a white solid: mp 121-123.5 °C; 1H NMR (300 MHz, DMSO-d6) δ 8.02 (d, J = 5.4 Hz, 1H), 7.28 (t, J =8.1 Hz, 1H), 7.22 (d, J = 8.5 Hz, 2H), 6.99-6.93 (m, 2H), 6.93-6.85 (m, 3H), 5.25 (s, 2H), 3.75 (s, 3H), 3.74 (s, 3H); MS (ESI) m/z 371 (M+H)+, 354 (M-NH2)".
Preparation of 0-allvl-N-(,5-fluoro-2-(3-methoxvbenzvloxv1Pvrimidin-4-vnhvdroxvlamine /321 /comparison): [0131]
[0132] To a mixture of 4-chloro-2-(3-methoxybenzyl)-5-fluoropyrimidine (0.151 g, 0.558 mmol) and O-allyl hydroxy-lamine hydrochloride (0.201 g, 1.83 mmol) in 5:1 MeOH:CH3CN (5 mL) was added triethylamine (0.273 g, 2.70 mmol) and the mixture was heated at 50 °C for18 h. The reaction was cooled to room temperature and diluted with Et20 (50 mL). The organic solution was washed with water (2 x 50 mL), dried over MgS04, filtered, and concentrated. Purification by flash chromatography (Si02, 17%—>50% EtOAc / hexane) afforded 0-allyl-N-(5-fluoro-2-(3-methoxybenzyloxy)-py-rimidin-4-yl)hydroxylamine (0.113 g, 66% yield) as a colorless oil: 1H NMR (300 MHz, DMSO-d6) δ 10.94 (broad singlet, 1H), 7.94 (broad singlet, 1H), 7.28 (t, J = 8.0 Hz, 1H), 6.95-7.03 (m, 2H), 6.88 (dd, J = 2.5, 7.9 Hz, 1H), 5.97 (tdd, J = 5.8, 10.6, 17.0 Hz, 1H), 5.32 (dd, J= 1.5, 17.4 Hz, 1H), 5.24 (s, 2H), 5.22 (dd, J= 1.2, 10.6 Hz, 1H), 4.39 (d, J=6.0 Hz, 2H), 3.74 (s, 3H); MS (ESI) m/z 306 (M+H)+, 304 (M-H)".
Preparation of 1-r2-(3-Cvanobenzvloxv1-5-fluoropvrimidin-4-vll-3-(2-fluorobenzvnurea (341 (comparison): [0133]
[0134] To a magnetically stirred mixture of 3-(4-amino-5-fluoropyrimidin-2-yloxymethyl)-benzonitrile (0.075 g, 0.31 mmol) and 2-fluorobenzylisocyanate (0.59 mL, 0.46 mmol) in dry DMF (1.5 mL) was added LiHMDS (1.0 M in THF, 0.31 ml, 0.30 mmol). The vial was capped and the mixture stirred at room temperature for 8 h. Saturated aq. NH4CI (3 ml) was added and the mixture was stirred for 4 h. The heterogeneous mixture was filtered, and the solid was washed with hot water, washed with E20, and then dried under vacuum to give the title compound (0.075 g, 62%) as a white solid: mp 177-178 °C; 1H NMR (400MHz, DMSO-d6) δ 10.04 (s, 1H), 8.90 (t, J= 5.7 Hz, 1H), 8.37 (d, J = 2.8 Hz, 1H), 7.85 (brs, 1H), 7.80 (d, J= 7.5 Hz, 1H), 7.74 (d, J= 8.0 Hz, 1H), 7.60 (t, J= 7.8 Hz, 1H), 7.42-7.38 (m,1H), 7.35-7.29 (m, 1H), 7.20-7.14 (m, 2H), 5.33 (s, 2H), 4.49 (d, J= 5.8 Hz, 2H); HPLC-MS (ESI) m/z 396.3 (M+H)+, 394.3 (M-H)-.
Preparation of 1-r5-Fluoro-2-(3-methoxvbenzvloxv1pvrimidin-4-vl1(3’-propvl carbamovh-3-propvl-urea(361(comparison1: [0135]
[0136] To a magnetically stirred mixture of 5-fluoro-2-(3-methoxybenzyloxy)pyrimidin-4-ylamine (0.075 g, 0.30 mmol) and propylisocyanate (0.057 mL, 0.60 mmol) in dry DMF (1.5 mL) was added LiHMDS (1.0 M in THF, 0.60 ml, 0.60 mmol). The vial was capped and the reaction was stirred at room temperature for 8 h. The solvent was evaporated under reduced pressure and the crude material was purified by reverse-phase chromatography to give the title compound (0.043 g, 10%) as a tan solid: mp 75-78 °C; 1H NMR (400MHz, DMSO-d6) δ 12.34 (s, 1H), 8.49 (s, 1H), 7.89 (s, 1H), 7.29 (t, J= 7.8 Hz, 1H), 7.05-7.01 (m, 2H), 6.90 (dd, J= 6.9Hz, J = 2.5 Hz, 1H), 5.30 (s, 2H), 3.75 (s, 3H), 3.74-3.68 (m, 2H), 3.15-3.10 (m, 2H), 1.58-1.44 (m, 4H), 0.89-0.85 (m, 6H); HPLC-MS (ESI) m/z 420.4 (M+H)+, 418.4 (M-H)-.
Preparation of 1-r2-(3-Cvanobenzvloxv)-5-fluoropvrimidin-4-vl1-3-propylthiourea (37)(comparison): [0137]
[0138] To a magnetically stirred mixture of 3-(4-amino-5-fluoropyrimidin-2-yloxymethyl)-benzonitrile (0.075 g, 0.31 mmol) and propylisothiocyanate (0.047 mL, 0.46 mmol) in dry DMF (1.5 mL) was added LiHMDS (1.0 M in THF, 0.31 ml, 0.31 mmol). The vial was capped and reaction was stirred for 8 h. Saturated aq NH4CI (3 ml) was added to the vial and the mixture was stirred for 4 h. The heterogeneous mixture was filtered and the solid was washed with hot water, washed with hexanes, and dried under vacuum to give the title compound (0.055 g, 52%) as a pale-yellow solid: mp 163-165 °C; 1H NMR (400MHz, DMSO-d6) δ 10.77 (s, 1H), 10.38 (s, 1H), 8.47 (d, J = 2.7 Hz, 1H), 7.90 (s, 1H), 7.82 (d, J = 7.5 Hz, 1H), 7.78 (d, J = 8.1 Hz, 1H), 7.62 (t, J = 7.7 Hz, 1 H), 5.42 (s, 2H), 3.55 (dd, J = 12.4, 6.8 Hz, 2H), 1.65-1.59 (m, 2H), 0.95 (t, J = 7.5 Hz, 3H): HPLC-MS (ESI) mlz 346.3 (M+H)+, 344.2 (M-H)’.
Preparation of N-i5-Fluoro-2-(,4-methvlbenzvloxv’)pvrimidin-4-vl1methanesulfonamide (381 (comparison'): [0139]
[0140] To a solution of 5-fluoro-2-(4-methylbenzyloxy)pyrimidin-4-ylamine (0.100 g, 0.43 mmol) in anhydrous THF (4 mL) was added LiHMDS (1.07 mL of 1,0M, 1.07 mmol) dropwise at room temperature, and the resulting orange solution was stirred for 20 min. Methanesulfonyl chloride (0.108 g, 0.94 mmol) was added in one portion and the turbid, light orange solution was stirred for 60 min. The reaction was quenched with brine (5 mL) and the THF phase was separated. The aq. phase was extracted w/ EtOAc (5 mL), and the organics were combined, dried over Na2S04, filtered, and concentrated to an orange gummy residue. The residue was purified by flash chromatography (Si02, 0—>100% EtOac / hexanes) to give 0.034 g (26%) of the title compound as a white solid: mp 145-148 °C; 1H NMR (400MHz, CDCI3) δ 8.19 (s, 1H), 7.33 (d, J= 7.9 Hz, 2H), 7.17 (d, J = 7.9 Hz, 2H), 5.35 (s, 2H), 3.37 (s, 3H), 2.35 (s, 3H); HPLC-MS (ESI) mlz 312 (M+H)+, 310 (M-H)-.
Preparation of N-i5-Fluoro-2-f4-fluorobenzvloxv)-Pvrimidin-4-vl1-S-(2-nitrophenvl’)-thiohvdroxvlamine (391(comparison'): [0141]
[0142] To a solution of 5-fluoro-2-(4-fluorobenzyloxy)pyrimidin-4-ylamine (0.05 g, 0.2mmol) and a 1.0 M solution of KOfBu in fBuOH (1.0 mL, 1.0 mmol) was added nitrobenzene-sulfenyl chloride (0.044 g, 0.23 mmol) in one portion, and the resulting brown solution was stirred for 60 min. The reaction was diluted with water (2 mL) and neturalized to pH 7 with 1N HCI. The aq. phase was extracted with EtOAc (5 mL), and the organics were combined, dried over Na2S04, filtered, and concentrated. The crude material was purified by reverse phase chromatography to yield the title compound (0.020 g, 26%) as a yellow solid: mp 184 °C; 1H NMR (300MHz, CDCI3) δ 8.36 (d, J= 7.25 Hz, 1H), 8.09 (d, J = 2.3 Hz, 1H), 7.59 (m, 1H), 7.36 (m 2H), 7.29 (m, 2H), 6.88 (m, 2H), 6.23 (bs, 1H), 5.19 (s, 2H); HPLC-MS (ESI) mlz 391(M+H)+, 389 (M-H)-.
Preparation of benzenesulfonic acid 4-acetvlamino-5-fluoro-pvrimidin-2-vl ester (40)(comparison): [0143]
[0144] N-(5-fluoro-2-hydroxypyrimidin-4-yl)-acetamide* (200 mg, 1.17 mmol) was suspended in pyridine (5 mL) and stirred at ambient temperature. To the stirred suspension was added benzenesulfonyl chloride (226 mg, 1.29 mmol) and agitation was continued for 16 hours. The solvent was evaporated under a stream of nitrogen and the residue was suspended in dichloromethane (2-3 mL), placed directly onto a silica gel column, and eluted with ethyl acetate in petroleum ether (0-50% gradient) to isolate 180 mg, 0.58mmol (49%) of the title compound as a white solid: mp 142-143 °C; 1H NMR (DMSO-d6) δ 10.96 (s, 1H), 8.67 (d, J= 2.6 Hz, 1H), 8.12-8.06 (m, 2H), 7.86-7.79 (m, 1H), 7.73-7.65 (m, 2H), 2.98 (s, 3H); HPLC-MS (ESI) m/z 312 (M+H)+, 310 (M-H)-. * N-(5-fluoro-2-hydroxypyrimidin-4-yl)-acetamide can be prepared through known literature methods. 1. Duschinsky, R„ Fells, E„ Hoffer, M. US Patent 3,309,359
Preparation of 2.2-dimethvlpropionic acid 4-(dimethvlamino-methvleneamino1-5-fluoro-pvrimidin-2-vloxvmethvl ester (411(comparison'): [0145]
[0146] N’-(5-fluoro-2-hydroxypyrimidin-4-yl)-N,N-dimethylformamidine (100 mg, 0.54 mmol), cesium carbonate (196 mg, 0.60 mmol), and chloromethyl pivalate (90 mg, 0.6 mmol) were shaken together in DMF (3 mL) at ambient temperature for 16 hours. The reaction mixture was partitioned between ethyl acetate and water, dried over magnesium sulfate, filtered and evaporated to yield a colorless oil which was treated with diethyl ether (3-4 mL) to produce a solid. The solid was removed and the ether solution was placed onto a silica gel column and eluted with ethyl acetate in petroleum ether (0-50% gradient) to isolate 14 mg, 0.05 mmol (9%) of the title compound as a white solid: mp 86-88 °C; 1H NMR(CDCI3) 68.73 (s, 1H),8.06 (d, J=2.6 Hz, 1H), 6.04 (s, 2H), 3.20(s, 3H), 3.18(s, 3H), 1.16 (s, 9H); HPLC-MS (ESI) m/z299(M+H)+.
Preparation of N’-(5-fluoro-2-methoxvmethoxvpvrimidin-4-vn-N.N-dimethvl-formamidine (421(comparison1: [0147]
[0148] N’-(5-fluoro-2-hydroxypyrimidin-4-yl)-N,N-dimethylformamidine (100 mg, 0.54 mmol), cesium carbonate (196 mg, 0.60 mmol), and bromomethyl methyl ether (75 mg, 0.6 mmol) were shaken together in DMF (3 mL) at ambient temperature for 4 hours. The reaction mixture was partitioned between ethyl acetate and water, dried over magnesium sulfate, filtered and evaporated to yield a colorless oil which was placed directly onto a silica gel column and eluted with ethyl acetate in petroleum ether (0-80% gradient) to isolate 23mg, 0.1 mmol (19%) of the title compound as a colorless oil: 1H NMR (CDCI3) δ 8.66 (s, 1H), 8.05 (d, J=2.6Hz, 1H), 5.46 (s, 2H), 3.53 (s, 3H), 3.17 (s, 3H), 3.16 (s, 3H); HPLC-MS (ESI) m/z 229 (M+H)+.
Preparation of [5-Fluoro-2-(3-methoxvbenzvloxv)pyrimidin-4-vl1sulfamide (43)(comparison): [0149]
[0150] To a magnetically stirred solution of 4-chloro-5-fluoro-2-(3-methoxybenzyloxy) pyrimidine* (1.3g, 4.84 mmol) in dry DMF (5mL) was added a pre-mixed suspension of 60% NaH (0.45 g, 10.65 mmol) and sulfamide (0.93g, 9.68 mmol) in dry DMF (5mL). The resulting off-white suspension was stirred at room temperature for 72hrs. The orange suspension was then heated to 50°C for 48 hours and cooled to room temperature. The reaction mixture was partitioned between ethyl acetate and brine solution. The organic extract was dried over Na2S04, filtered, and evaporated. The crude material was purified by column chromatography on normal phase silica using a gradient of EtOAc/Hex and reverse phase using a gradient of H20/ACN to yield [5-Fluoro-2-(3-methoxybenzyloxy) pyrimidin-4-yl]sulfamide (115 mg, 7.2% yield) as a white solid: mp 126-130 °C; 1H NMR(300MHz, CD3OD) δ 8.01 (d, J= 3.63 Hz, 1H), 7.25 (m, 1H), 7.01 (m, 2H), 6.88 (m, 1H), 5.37 (s, 2H), 3.78 (s, 3H); MS (ESI) mlz 326.9 (M-H)-. * The 4-chloro-5-fluoro-2-(3-methoxybenzyloxy) pyrimidine intermediate was prepared as described in the synthesis of 31.
Preparation of 5-fluoro-4-hvdrazinvl-2-(3-methoxvbenzvloxv1pvrimidine (441 (comparison^ [0151]
[0152] A 125 mL Erlenmeyer flask was charged with 4-chloro-5-fluoro-2-(3-methoxybenzyl-oxy)pyrimidine (1.50 g, 5.58 mmol) and EtOH (50 mL). Hydrazine monohydrate (900 μί, 18.5 mmol) was added, and the resulting mixture was allowed to stir at room temperature. After 22 h, the reaction was transferred to a 500 mL Erlenmeyer flask and diluted with water (200 mL), whereupon a white solid began to precipitate from solution. After stirring for 7 h, solid product was collected in a fritted funnel and rinsed with excess water. After drying on the frit, the title compound was obtained (1.23 g, 83%) as a white solid: mp 103-106 °C; 1H NMR (300 MHz, DMSO-d6) δ 8.92 (bs, 1H), 7.86 (d, J = 3.6 Hz, 1H), 7.27 (t, J = 8.1 Hz, 1H), 6.94 - 7.01 (m, 2H), 6.87 (dd, J = 2.4, 7.9 Hz, 1H), 5.24 (s, 2H), 4.46 (bs, 2H), 3.74 (s, 3H); MS (ESI) mlz 265.2 (M+H)+, 263.2 (M-H)-.
Preparation of (E1-5-Fluoro-2-(3-methoxvbenzvloxv')-4-(2-(thiophen-2-vlmethvlene1-hvdrazinvl')pvrimidine(451(compar-isonl: [0153]
[0154] A 20 mL vial was charged with 5-fluoro-4-hydrazinyl-2-(3-methoxybenzyloxy)-pyrimidine(74.7 mg, 0.283 mmol), EtOH (2 mL), thiophene-2-carbaldehyde (26 μί, 0.284 mmol) and 1 M HCI in Et20 (14 μί, 0.014 mmol) and heated at 50 °C on shaker. After 90 minutes, the reaction was cooled to room temperature concentrated on high vacuum to provide the title compound (77.8 mg, 77%) as a yellow solid: mp 136-139 °C; 1H NMR (300 MHz, DMSO-d6) δ 11.46 (bs, 1H), 8.50 (bs, 1H), 8.16 (d, J = 3.6 Hz, 1H), 7.64 (d, J= 5.0 Hz, 1H), 7.41 (d, J= 3.4 Hz, 1H), 7.28 (t, J= 8.0 Hz, 1H), 7.12 (dd, J = 3.8, 4.8 Hz, 1H), 7.04 (m, 2H), 6.88 (dd, J = 2.4, 8.3 Hz, 1H), 5.27 (s, 2H), 3.73 (s, 3H); MS (ESI) mlz 359.2 (M+H)+, 357.2 (M-H)-.
Preparation of 2-(benzvloxv)-4-[(dimethvl-X4-sulfanylidene)amino1-5-fluoropvrimidine (47)(comparison): [0155]
[0156] A 10 mL oven-dried Schlenk flask was charged with 2-(benzyloxy)-5-fluoropyrimidin-4-amine (101 mg, 0.462 mmol), CH2CI2 (2 mL), and dimethylsulfide (75.0 μί, 1.02 mmol) and was cooled to 0 °C in an ice bath. A/-Chlorosuc- cinimide (122 mg, 0.914 mmol) was added and the resulting mixture was allowed to stir at 0 °C for 45 minutes, and then at room temperature for 30 minutes. A solution of NaOMe in MeOH (25% , 360 μΙ_, 1.35 mmol) was added. After 20 minutes, the reaction was quenched with water (3 mL) and allowed to stir for 1 hour. The crude reaction mixture was then diluted with CH2CI2 and washed with water (50 mL x2), dried over anhydrous Na2S04, filtered, and concentrated by rotary evaporation and then on high vacuum to give the title compound (120 mg, 93%) as an off white solid: mp 125-129 °C; 1H NMR(300MHz, DMSO-d6): δ 7.70 (d, J = 3.9 Hz, 1H), 7.25-7.44 (m, 5H), 5.21 (s,2H),2.75 (s, 6H); MS (ESI) mlz 281.1 (M+H)+. ‘Yamamoto, Y.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 4128-4129.
Preparation of 1-r5-fluoro-2-(4-methvlbenzvloxvVpvrimidin-4-vl1-2.3-dipropvl-isothiourea (491(com parison): [0157]
[0158] To a magnetically stirred solution of 1-[5-Fluoro-2-(4-methyl-benzyloxy)-pyrimidin-4-yl]-3-propyl-thiourea (0.50 g, 1.40 mmol) in CH3CN (4 mL), was added potassium carbonate (0.20 g, 1.40 mmol) at room temperature and the mixture was stirred for 20 min. A/-Propylbromide (0.19 g, 1.40 mmol) was added at room temperature and the resulting mixture stirred for 15 h. The reaction mixture was diluted with H20 and extracted with CH2CI2 (3x20 mL). The combined organic layers were dried over Na2S04, filtered, and the solvent evaporated. The crude mixture was purified on silica (EtOAc/hexanes gradient) and evaporation of the product fractions gave 0.335 g (63 %) of 1-[5-Fluoro-2-(4-methyl-benzyloxy)-pyrimidin-4-yl]-2,3-dipropyl-isothiourea as a pale yellow viscous liquid: 1FI NMR (300MHz, CDCI3) δ 10.56 (bs, 1H), 8.09 (d, J = 2.6 Hz, 1H), 7.31 (m, 2H), 7.24 (m, 2H), 5.28 (s, 2H), 3.28 (dd, J= 13.6, 6.5 Hz, 4H), 2.36 (s, 3H), 1.62 (m, 4H), 1.0 (t, J = 7.4 Hz, 4H); HPLC-MS (ESI) mlz 377(M+H)+.
Preparation of 0-(4-amino-5-fluoropvrimidin-2-vlW-butvl A/-methvl-A/-hvdroxvcarbamate (501 [0159]
[0160] In a 2 dram screw cap vial, a solution of 4-amino-2-chloro-5-fluoropyrimidine (0.1 g, 0.68 mmol) and f-butyl N-methyl-N-hydroxycarbamate * (0.11 g, 0.75 mmol) was treated with a 1.0 M solution of KOfBu in fBuGH (1.0 mL, 1.0 mmol) in one portion, and the resulting yellow solution was heated at 100 °C and shaken for 24 h. The reaction mixture was cooled, extracted with EtOAC (3x5 mL), and the solvent evaporated. The crude mixture was purified via reverse phase chromatography to yield 0.10 g (56.9%) of the title compound as yellow solid: mp 123-125 °C; 1H NMR (300MHz, CDCI3) δ 7.96 (d, J = 2.3 Hz,1H), 5.26 (bs, 2H), 3.32 (s, 3H), 1.43 (s, 9H); MS (ESI) mlz 259 (M+H)+. * f-butyl A/-methyl-A/-hydroxycarbamate can be prepared through known literature methods: 1. Carrasco, M. R.; Brown, R. T.; Serafimova, I. M.; Silva O. J. Org. Chem., 2003, 68 (1), 195.
Preparation of O-ethvI 5-fluoro-2-(4-fluorobenzvloxv)pyrimidin-4-vlcarbamothioate (51)(comparison): [0161]
[0162] 5-fluoro-2-(4-fluorobenzyloxy)pyrimidin-4-amine (300 mg, 1.26 mmol) was stirred in chloroform (25 mL) and water (12 mL). Sodium bicarbonate (870 mg, 10.12 mmol) was added followed by dropwise addition of thiophosgene (218 mg, 1.9 mmol). The reaction mixture was stirred at room temperature for 16 hours, then diluted with chloroform (20 mL) and the phases were separated. The organic extract was dried over sodium sulfate, filtered, and concentrated by rotary evaporation to 1/3 volume. To this chloroform solution of crude isothiocyanate was added abs. ethanol (10 mL) and the mixture was heated in a sealed tube for 1h. The reaction mixture was cooled to room temperature, concentrated and purified by flash chromatography on silica, to give 45 mg (11%) of O-ethyl 5-fluoro-2-(4-fluorobenzy-loxy)pyrimidin-4-ylcarbamothioate as a pale yellow solid: mp 109-119 °C; 1H NMR (CDCI3) δ 8.30 (bs, 2H), 7.44 (m, 2H), 7.06 (m, 2H), 5.36 (s, 2H), 4.66 (q, J = 6 Hz, 2H), 1.45 (t, J = 6 Hz, 3H); HPLC-MS (ESI): m/z 326 (ES+).
Preparation of A/-(5-fluoro-2-(4-fluorobenzvloxv1pvrimidin-4-vhethanethioamide (53)(comparison1: [0163]
[0164] A/-(5-fluoro-2-(4-fluorobenzyloxy)pyrimidin-4-yl)acetamide (50 mg, 0.42 mmol) was stirred in a Biotage Initiator® microwave vessel with 1,2-dichloroethane (3 mL) and Lawesson’s reagent (170 mg, 0.42 mmol). The vessel was heated in a Biotage Initiator® microwave to 100 °C for 5 minutes then cooled room temperature, filtered, and diluted with CH2CI2. The reaction mixture was then washed brine, and the layers were separated. The organic extract was dried onto silica and purified by flash chromatography. The product-containing fractions were then evaporated to dryness and purified again by reverse-phase HPLC to give 4 mg of A/-(5-fluoro-2-(4-fluorobenzyl-oxy)pyrimidin-4-yl)ethanethioamide (4%) as a yellow glass: 1H NMR (CDCI3) δ 9.34 (b, 1H), 8.29 (d, J=3Hz, 1H), 7.41 (m, 2H), 7.06 (m,2H), 5.33 (s, 2H), 3.13 (s, 3H); HPLC-MS (ESI): mlz 294 (ES ).
Biological testing Protocols:
1. Evaluation of Fungicidal Activity: Leaf Blotch of Wheat (Mvcosphaerella araminicola: anamorph: Septoria tritici: Baver code SEPTTRT
[0165] Wheat plants (variety Yuma) were grown from seed in a greenhouse in 50% mineral soil/50% soil-less Metro mix until the first leaf was fully emerged, with 7-10 seedlings per pot. These plants were inoculated with an aqueous spore suspension of Septoria tritici either prior to or after fungicide treatments. After inoculation the plants were kept in 100% relative humidity (one day in a dark dew chamber followed by two to three days in a lighted dew chamber) to permit spores to germinate and infect the leaf. The plants were then transferred to a greenhouse fordisease to develop. 2. Evaluation of Fungicidal Activity: Leaf Spot of Sugar Beets (Cercospora beticola: Baver code CERCBE): [0166] Sugar beets (variety HH-88) were grown in soil-less Metro mix in a greenhouse. The spores were harvested from moisturized infected leaf surface by washing whole leaves in water, and then filtered through two layers of cheesecloth. The young seedlings were inoculated with the spore suspension. The plants were kept in a dark dew room for 48 hrs, and then placed under a plastic hood in a greenhouse with a temperature of 26 °C. 3. Evaluation of Fungicidal Activity: Leaf Spot of Peanut (Mvcosphaerella arachidis: Baver code MYCOAR: anamorph: Cercospora arachidicola): [0167] Peanuts seedlings (variety Star) were grown in soil-less Metro mix. The spores were harvested from moisturized infected leaf surface by washing whole leaves in water, and then filtered through two layers of cheesecloth. The young seedlings were inoculated with the spore suspension. The plants were kept in a dark dew room for 48 hrs, and then placed under a plastic hood in a greenhouse with a temperature of 26 °C. 4. Evaluation of Fungicidal Activity: Apple Scab (Venturia inaeaualis: Baver code VENTIN1: [0168] Apple seedlings (McIntosh or Golden Delicious) were grown in Metro mix in a greenhouse. Fungal spores were collected from infected leaf tissue. Plants were inoculated with the spore suspension. Plants were placed in a dew room for 24 hours with 100% relative humidity and then transferred to a greenhouse with a temperature of 18 °C for disease to develop. 5. Evaluation of fungicidal activity: Black Siaatoka Disease of Banana (Mvcosphaerella fiiiensis: BAYER code MYCOFO: [0169] Efficacy against Mycosphaerella fijiensis was tested using newly emerged leaves of field grown banana plants. 20 ml of a diluted formulation of compound 1 of the required concentration were sprayed onto each test leaf over a delineated area of 20 x 20 cm. The leaves were subsequently allowed to become infected by natural inoculum, and were visually assessed for percent disease control ~ 40 - 45 days later.
[0170] The following table presents the activity of typical compounds of the present disclosure when evaluated in these experiments. The effectiveness of the test compounds in controlling disease was determined by assessing the severity of disease on treated plants, then converting the severity to percent control based on the level of disease on untreated, inoculated plants.
[0171] In each case of Tables l-lll the rating scale is as follows:
TABLE I: 3 DC and 1 DP Activity of Compounds on SEPTTR at 25 and 100 ppm
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[0172] Examples 6, 7, 8, 9, 10, 11,12, 13, 14, 16, 17, 18, 19, 20,21,22, 23,24, 25, 26,27, 28, 30, 31,32, 34, 36, 37, 38, 39, 40, 41,42, 43, 44, 45, 47, 48, 49, 51, 52, 53, 54, 56, 58, 59, 62, 63, 64, 65, 67, 68, 71, 73, 75, 77, 80, 81, 84, 85, 86, 87, 88, 89, 90, 91,92, 94, 97, 98, 99, 101,102, 105, 107, 108, 110, 111, 112, 113, 114, 115, 116, 117, 118, 119, 121,122, 123, 124, 125, 126, 128, 130, 131,134, 135, 138, 140, 142, 143, 146, 147, 148, 149, 150, 151, 152, 153, 155, 157, 158, 159, 160, 161,162, 163, 164, 165, 166, 167, 168, 169, 170, 174, 176, 177, 179, 180, 182, 183, 186, 187, 191, 196, 198, 199, 200, 201,202, 203, 204, 205, 206, 208, 209, 214, 215, 216, 217, 218, 220, 222, 225, 226, 227, 228, 229, 230, 231,233, 234, 235, 237, 238, 239, 241,242, 243, 244, 245, 247, 248, 249, 252, 253, 254, 255, 257, 258, 259, 260, 261,262, 263, 264, 265, 266, 269, 272, 273, 274, 276, 277, 278, 279, 280, 281,282, 283, 285, 287, 288, 290, 291,292, 293, 294, 295, 297, 298, 299, 301,303, 304, 306, 309, 310, 314, 317, 318, 319, 321,322, 324, 325, 326, 327, 329, 330, 331,332, 333, 334, 336, 338, 339, 340, 343, 344, 346, 347, 349, 352, 353, 354, 357, 358, 359, 360, 361,362, 363, 364, 366, 367, 369, 371,373, 374, 375, 376, 377, 379, 380, 388, 389, 390, 394, 395, 397, 398, 402, 405, 407, 408, 410, 411, 412, 414, 415, 416, 417, 418, 419, 420, 421,422, 424, 425, 426, 427, 432, 434, 435, 438, 439, 440, 443, 444, 445, 446, 447, 448, 449, 451,452, 453, 454, 456, 457, 458, 459, 461,463, 464, 466, 467, 469, 470, 471,473, 475, 477, 478, 479, 480, 482, 483, 484, 485, 487, 490, 491,492, 493, 494, 495, 496, 497, 498, 499, 501,503, 504, 505, 506, 507, 512, 515, 516, 517, 518, 519, 520, 521, 523, 525, 527, 528,, 529, 530, 531, 532, 533, 534, 535, 536, 538, 539, 541, 542, 548, 550, 552, 553, 555, 556, 557, 558, 559, 561,562, 563, 565, 566, 567, 568, 570, 571,572, 575, 579, 585, 586, 587, 588, 589, 591,594, 595, 598, 599, 600, 601,603, 605, 606, 608, 610, 612, 613, 614, 615, 616, 618, 619, 620, 621,622, 624, 626, 627, 629, 633, 634, 636, 638, 639, 641, 642, 643, 646, 647, 649, 651 , 652, 654, 655, 656, 657, 658, 659, 661, 662, 663, 664, 665, 666, 667, 668, 669, 670, 672, 674, 675, 676, 677, 678, 679, 680, 681,683, 684, 685, 686, 688, 690, 692, 694, 695, 697, 700, 701,702, 703, 704, 706, 709, 711,712, 714, 717, 718, 720, 721,723, 724, 726, 727, 728, 729, 730, 732, 736, 737, 738, 739, 741,742, 744, 745, 749, 750, 751,753, 754, 755, 756, 758, 759, 760, 761,762, 765, 766, 767, 769, 770, 771,773, 774, 775, 776, 777, 778, 780, 781,782, 784, 785, 786, 788, 789, 791,792, 793, 795, 797, 799, 801 are for comparison only. TABLE 11:1 DP Activity of Compounds on SEPTTR at 50 and 200 ppm
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[0173] Examples 803, 804, 805, 806, 807, 808, 809, 810, 811, 812, 813, 814, 815, 816, 817, 818, 819, 820, 821,822, 823, 824, 825, 826, 827, 828, 829, 830, 831,832, 833, 834, 835, 836, 837, 838, 839, 840, 841,842, 843, 844, 845, 849, 851,852, 854, 855, 857, 858, 859, 860, 861,862, 863, 865, 866, 867, 868, 869, 870, 871,872, 873, 874, 875, 876, 877, 879, 880, 881,882, 883, 884, 885, 886, 887, 888, 889, 890, 892, 893, 894, 895, 896, 897, 898, 899, 900, 901,902, 903, 904, 905, 906, 907, 908, 909, 910, 911, 912, 913, 914, 915, 916, 917, 918, 919, 920, 921,922, 923, 924, 925, 926, 927, 928, 929, 930, 931,934, 935, 937, 938, 940, 941, 942, 943, 944, 945, 946, 947, 948, 949, 950, 951, 952, 953 are for comparison only. TABLE III: 1 DP Activity of Compounds
on CERCBE, VENTIN, and MYCOFI (continued)
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[0174] Examples 6, 7, 8, 9, 10, 11,12, 13, 14, 16, 17,18, 19, 20, 21,22, 23, 24, 25, 26, 27, 28, 30, 31,32, 34, 36, 37, 38, 39 40, 41,42, 43, 44, 45, 47, 48, 49, 51,52, 53, 54, 56, 58, 59, 62, 63, 64, 65, 67, 68, 71,73, 75, 77, 80, 81, 84, 85, 86, 87, 88, 89, 90, 91,92, 94, 97, 98, 99, 101, 102, 105, 107, 108, 110, 111, 112, 113, 114, 115, 116, 117, 118, 119, 121,122, 123, 124, 125, 126, 128, 130, 131,134,135,138,140,142,143, 146,147,148,149,150,151, 152,153,155, 157, 158, 159, 160, 161,162, 163, 164, 165,166,167,168,169,170,174, 176,177,179,180,182,183, 186,187,191, 196, 198, 199, 200, 201,202, 203, 204, 205, 206, 208, 209, 214, 215, 216, 217, 218, 220, 222, 225, 226, 227, 228, 229, 230, 231,233, 234, 235, 237, 238, 239, 241,242, 243, 244, 245, 247, 248, 249, 252, 253, 254, 255, 257, 258, 259, 260, 261,262, 263, 264, 265, 266, 269, 272, 273, 274, 276, 277, 278, 279, 280, 281,282, 283, 285, 287, 288, 290, 291,292, 293, 294, 295, 297, 298, 299, 301,303, 304, 306, 309, 310, 314, 317, 318, 319, 321,322, 324, 325, 326, 327, 329, 330, 331,332, 333, 334, 336, 338, 339, 340, 343, 344, 346, 347, 349, 352, 353, 354, 357, 358, 359, 360, 361,362, 363, 364, 366, 367, 369, 371,373, 374, 375, 376, 377, 379, 380, 388, 389, 390, 394, 395, 397, 398, 402, 405, 407, 408, 410, 411, 412, 414, 415, 416, 417, 418, 419, 420, 421,422, 424, 425, 426, 427, 432, 434, 435, 438, 439, 440, 443, 444, 445, 446, 447, 448, 449, 451,452, 453, 454, 456, 457, 458, 459, 461,463, 464, 466, 467, 469, 470, 471,473, 475, 477, 478, 479, 480, 482, 483, 484, 485, 487, 490, 491,492, 493, 494, 495, 496, 497, 498, 499, 501,503, 504, 505, 506, 507, 512, 515, 516, 517, 518, 519, 520, 521,523, 525, 527, 528, 529, 530, 531,532, 533, 534, 535, 536, 538, 539, 541,542, 548, 550, 552, 553, 555, 556, 557, 558, 559, 561,562, 563, 565, 566, 567, 568, 570, 571,572, 575, 579, 585, 586, 587, 588, 589, 591,594, 595, 598, 599, 600, 601,603, 605, 606, 608, 610, 612, 613, 614, 615, 616, 618, 619, 620, 621,622, 624, 626, 627, 629, 633, 634, 636, 638, 639, 641,642, 643, 646, 647, 649, 651,652, 654, 655, 656, 657, 658, 659, 661,662, 663, 664, 665, 666, 667, 668, 669, 670, 672, 674, 675, 676, 677, 678, 679, 680, 681,683, 684, 685, 686, 688, 690, 692, 694, 695, 697, 700, 701,702, 703, 704, 706, 709, 711,712, 714, 717, 718, 720, 721,723, 724, 726, 727, 728, 729, 730, 732, 736, 737, 738, 739, 741,742, 744, 745, 749, 750, 751,753, 754, 755, 756, 758, 759, 760, 761,762, 765, 766, 767, 769, 770, 771,773, 774, 775, 776, 777, 778, 780, 781,782, 784, 785, 786, 788, 789, 791,792, 793, 795, 797, 799, 801,803, 804, 805, 806, 807, 808, 809, 810, 811, 812, 813, 814, 815, 816, 817, 818, 819, 820, 821, 8.22, 823, 824, 825, 826, 827, 828, 829, 830, 831,832, 833, 834, 835, 836, 837, 838, 839, 840, 841, 842, 843, 844, 845, 849, 851,852, 854, 855, 857, 858, 859, 860, 861,862, 863, 865, 866, 867, 868, 869, 870, 871,872, 873, 874, 875, 876, 877, 879, 880, 881,882, 883, 884, 885, 886, 887, 888, 889, 890, 892, 893, 894, 895, 896, 897, 898, 899, 900, 901,902, 903, 904, 905, 906, 907, 908, 909, 910, 911,912, 913, 914, 915, 916, 917, 918, 919, 920, 921,922, 923, 924, 925, 926, 927, 928, 929, 930, 931, 934, 935, 937, 938, 940, 941,942, 943, 944, 945, 946, 947, 948, 949, 950, 951,952, 953 are for comparison only.
Claims
1. A compound of formula I wherein R1 is -N(R3)R4;
R2 is -OR21; R3 is: H; R4 is: H; R8 is independently C^Cg alkyl, C^Cg haloalkyl, amino, C^Cg alkylamino, C2-C6 dialkylamino, phenyl optionally substituted with 1-3 R30, or a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11; R11 is independently halogen, CrCg alkyl, C-|-C6 haloalkyl, C-j-Cg alkoxy, CrCg haloalkoxy, C-pCg alkylthio, C-j-Cg haloalkylthio, amino, C-pCg alkylamino, C2-C6 dialkylamino, C2-C6 alkoxycarbonyl, or C2-C6 alkylcarbonyl; R20 is independently halogen, cyano, nitro, amino, C-pCg alkoxyalkoxy, C-pCg alkyl, C-pCg haloalkyl, C-pCg hydroxy-alkyl, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, hydroxyl, C-|-C6 alkoxy, CrC6 haloalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 haloalkynyloxy, C^Cg alkylthio, C^Cg haloalkylthio, C-j-Cg alkylsulfonyl, C1-C6 haloalkylsulfonyl, C2-C6 alkenylthio, C2-C6 haloalkenylthio, C2-C6 haloalkenylsulfonyl, C3-C6 alkynylthio, C3-C6 alkynylsulfonyl, C3-C6 haloalkynylsulfo-nyl, CrC6 alkylamino, C2-C8 dialkylamino, C3-C8 dialkylaminocarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C3-C6trialkylsilyl,2-[(E)-methoxyimino]-N-methyl-acetamidyl, phenyl, benzyl, benzyloxy, phenoxy,ora5-or6-mem-bered heteroaromatic ring wherein each phenyl, benzyl, benzyloxy, phenoxy, or 5- or 6- membered heteroaromatic ring may be optionally substituted with 1-3 substitutents independently selected from R31; R21 is: C.|-C14 alkyl; C^Cg haloalkyl; C2-C4 alkenyl; C2-C4 haloalkenyl; C3-C4 alkynyl; C3-C4 haloalkynyl; phenyl, naphthyl, or tetrahydroquinolinyl each optionally substituted with 1-3 R20; -(CHR22)mR23. -(CHR24)mC(0)0R25; -(CHR24)mC(0)R26; -(CHR24)mC(0)N(R27)R28; -(CHR24)mOR29; -(CHR24)mSR29 -(CHR24)mN(R27)R28; -C(=0)R32; -N=C(R32)(R36). -NR25C(5=0)0R2s -Si(R8)3; -S02R33; C2-C6 alkoxy carbonyl; C2-C6 alkylaminocarbonyl; C2-C6 alkylcarbonyl; sugars selected from the group consisting of beta-D-glucose-tetraacetate, rhamnose, fructose, and pentose; or a 5- or 6- membered heteroaromatic ring selected from the group consisting of furanyl, pyridinyl, pyridinyl-N-oxide, pyrimidinyl, pyridazinyl, pyrazinyl, pyrazolyl,thiazolyl,triazinyl,thiadiazolyl,oxazolyl,triazolylorisoxazolyl wherein each 5- or 6- member heteroaromatic ring may be optionally substituted with 1-5 R20; wherein m is an integer from 1-3; R22 is independently: H; halogen; cyano; nitro;
CrC6 alkyl; C.|-Cg haloalkyl; phenyl or benzyl optionally substituted with 1-3 R20 C-pCg hydroxyalkyl; C2-C6 alkoxylalkyl; C3-C6 haloalkynyl; C2-C6 alkenyl; C2-C6 haloalkenyl; C3-C6 alkynyl; C^Cg alkoxy; C^Cg haloalkoxy; C^Cg alkylthio; C^Cg alkylamino; C2-C8 dialkylamino; C3-C6 cycloalkylamino; C4-C6 (alkyl)cycloalkylamino; C2-C6 alkylcarbonyl; C2-C6 alkoxycarbonyl; C2-C6 alkylaminocarbonyl; C3-C8 dialkylaminocarbonyl; C3-C6 trialkylsilyl; ring-fused heteroaromatic rings selected from the group consisting of benzothiophenyl, quinolinyl, isoquinolinyl, thieno[2,3-b]pyridyl, 1-methyl-1 H-thieno[2,3-c]pyrazolyl, and benzoimidazolyl, wherein each of the rings may be further substituted with 1-3 R20; or a 5- or 6- membered heteroaromatic ring selected from the group consisting of furanyl, pyridinyl, pyridinyl-N-oxide, pyrimidinyl, pyridazinyl, pyrazinyl, thiazolyl, triazinyl, thiadiazolyl, oxazolyl, isoxazolyl, triazolyl and thienyl; R23 is: H; halogen; G-|-Og alkyl; C-pCg haloalkyl; C2-C6 dialkylamino; phenyl optionally substituted with 1-5 R20; ring-fused heteroaromatic rings selected from the group consisting of benzothiophenyl, quinolinyl, isoquinolinyl, thieno[2,3-b]pyridyl, 1-methyl-1 H-thieno[2,3-c]pyrazolyl, benzofuranyl and benzoimidazolyl, 2,3-dihydro-ben-zofuran-2-yl, 4-methyl-4H-thieno[3,2-b]pyrrol-5-yl, 1-methyl-1H-indol-5-yl, imidazo[1,2-a]pyridin-2-yl, imida-zo[2,1-b]thiazol-6-yl, benzothiazol-2-yl, benzo[b]thiophen-7-yl, and 1-methyl-1 H-indazol-3-yl, wherein each of the rings may be further substituted with 1-3 R20; naphthyl; benzo[1,3]dioxolyl; pyrrolidinonyl; oxetanyl; C-j-Cg alkylthio optionally substituted with 1-5 R20; a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11; or a 5- or 6- membered heteroaromatic ring selected from the group consisting of furanyl, pyridinyl, pyridinyl-N-oxide, pyrimidinyl, pyridazinyl, pyrazinyl, pyrazolyl, thiazolyl, triazinyl, thiadiazolyl, oxazolyl, isoxazolyl, triazolyl, imidazolyl, thiophene-2-yl and thiophen-3-yl wherein each heteroaromatic ring may be optionally substituted with 1-3 R20; R24 is H, C-pCg alkyl, C-pCg alkoxy, benzyl, or phenyl wherein each of the benzyl or phenyl may be optionally substituted with 1-3 R20; R25 is H, C.|-Cg alkyl, phenyl or benzyl optionally substituted with 1-3 R20; R26 is: H;
CrCg alkyl; C^Cg alkoxy; phenyl optionally substituted with 1-3 R20; or a 5- or 6 membered heteroaromatic ring selected from the group consisting of furanyl, pyridinyl, pyridinyl-N-oxide, pyrimidinyl, pyridazinyl, pyrazinyl, thiazolyl, triazinyl, thiadiazolyl, oxazolyl, triazolyl and isoxazolyl; R27 and R28 are independently: H; C-pCg alkyl; benzyl or phenyl wherein each of the benzyl or phenyl may be optionally substituted with 1-3 R20 ; or a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11; R29 is: H; C^Cg alkyl; C^Cg haloalkyl; C^Cg alkoxyalkyl; C2-C6 alkylcarbonyl; benzyl or phenyl wherein each of the benzyl or phenyl may be optionally substituted with 1-3 R20; or a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11; R89 is independently halogen, cyano, nitro, CrC6 alkyl, CrC6 haloalkyl, CrCg hydroxyalkyl, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, hydroxyl, C-|-C6 alkoxy, CrC6 haloalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 haloalkynyloxy, C-pCg alkylthio, CrC6 alkylsulfonyl, C^Cg haloalkylsulfonyl, C2-C6 alkenylthio, C2-C6 haloalkenylthio, C2-C6 haloalkenylsulfonyl, C3-C6 alkynylthio, C3-C6 alkynylsulfonyl, C3-C6 haloalkynylsulfonyl, C-pCg alkylamino, C2-C8 dialkylamino, C3-C8 dialkylaminocarbonyl, C3-C6 trialkylsilyl, thiazolyl, phenyl, pyrimidinyl, or pyridyl, wherein the thiazolyl, phenyl, pyridyl, or pyrimidinyl may be optionally substituted with 1-3 R20; R31 is independently halogen, cyano, nitro, C^Cg alkyl, C-j-Cg haloalkyl, C-j-Cg hydroxyalkyl, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, hydroxyl, C^Cg alkoxy, CrC6 haloalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 haloalkynyloxy, C-j-Cg alkylthio, C^Cg alkylsulfonyl, C^Cg haloalkylsulfonyl, C2-C6 alkenylthio, C2-C6 haloalkenylthio, C2-C6 haloalkenylsulfonyl, C3-C6 alkynylthio, C3-C6 alkynylsulfonyl, C3-C6 haloalkynylsulfonyl, C-pCg alkylamino, C2-C8 dialkylamino, C3-C8 dialkylaminocarbonyl, or C3-C6 trialkylsilyl; R32 is independently:
CrCg alkyl, CrCg haloalkyl, CrCg hydroxyalkyl, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, hydroxyl, C1-C6 alkoxy, C-pCg haloalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 haloalkynyloxy, C.|-Cg alkylthio, C^Cg alkylsulfonyl, C-pCg haloalkylsulfonyl, C2-C6 alkenylthio, C2-C6 haloalkenylthio, C2-C6 haloalkenylsulfonyl, C3-C6 alkynylthio, C3-C6 alkynylsulfonyl, C3-C6 haloalkynylsulfonyl, CrC6 alkylamino, C2-C8 dialkylamino, C3-C8 dialkylaminocarbonyl, C3-C6 trialkylsilyl; phenyl wherein the phenyl ring may be optionally substituted with 1-3 R20; or a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11; R33 is independently:
CrCg alkyl, CrC6 haloalkyl, phenyl or thienyl optionally substituted with 1-3 R20; or a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11; R34 is:
CrCg alkyl, C^Cg haloalkyl, C2-C6 alkoxyalkyl, CrC6 alkylamino; or a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11; R35 is: C-pCg alkyl, C2-C6 alkylcarbonyl; or a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11; R36 is H, cyano, CrC6 alkyl, CrC6 alkoxy, benzyl, or phenyl wherein each of the benzyl or phenyl may be optionally substituted with 1-3 R20; alternatively R32 and R36 may be taken together to form: a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11; and R37 is independently: H, halogen, or phenyl optionally substituted with 1-5 R20;
CrC6 alkyl, CrC6 haloalkyl, hydroxyl, C-j-Cg alkoxy, or C-j-Cg haloalkoxy; or a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11, with the proviso that the compound is not 4-amino-5-fluoro-2-tri-C1-C7-alkyl-silyloxypyrimidine, 2-ethoxy-4-ami-no-5-fluoropyrimidine or 2-methoxy-4-amino-5-fluoropyrimidine. 2. The compound of the formula I according to Claim 1 wherein R3 is H; R4 is H, R21 is -C(=0)R32, -N=C(R32)(R36), -S02R33, NR25C(=0)0R25, CrCg alkyl, C-j-Cg alkoxy, R25 is H, C-j-Cg alkyl, R32 is C1-C6 alkyl, phenyl wherein the phenyl may be optionally substituted with 1-3 R20, R33 is CrC6 alkyl, phenyl or thienyl optionally substituted with 1-3 R20, R36 is cyano, C.|-Cg alkyl, phenyl wherein the phenyl may be optionally substituted with 1-3 R20, and R20 is halogen, C^Cg alkyl, C.|-Cg alkoxy. 3. The compound of the formula I according to Claim 1 wherein R3 is H; R4 is H, R21 is (-CHR22)mR23, m is 1, R22 is H, C1-C4 alkyl, phenyl, R23 is a ring-fused heteroaromatic rings selected from the group consisting of benzothiophenyl, quinolinyl, isoquinolinyl, thieno[2,3-b]pyridyl, 1-methyl-1H-thieno[2,3-c]pyrazolyl, benzofuranyl and benzoimidazolyl, 2,3-dihydro-benzofuran-2-yl, 4-methyl-4H-thieno[3,2-b]pyrrol-5-yl, 1-methyl-1 H-indol-5-yl, imidazo[1,2-a]pyridin-2-yl, imidazo[2,1-b]thiazol-6-yl, benzothiazol-2-yl, benzo[b]thiophen-7-yl, 1-methyl-1 H-indazol-3-yl, wherein each of the rings may be further substituted with 1-3 R20, R20 is halogen, C-j-Cg alkyl, C-j-Cg alkoxy. 4. The compound of the formula I according to Claim 1 wherein R3 is H; R4 is H, R21 is (-CHR22)mR23, m is 1, R22 is H, R23 is a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11. 5. The compound of the formula I according to Claim 1 wherein R3 is H; R4 is H, R21 is (-CHR22)mR23, m is 1, R22 is H, R23 is a 5- or 6- membered heteroaromatic ring selected from the group consisting of furanyl, pyridinyl, pyridinyl-N-oxide, pyrimidinyl, pyridazinyl, pyrazinyl, pyrazolyl, thiazolyl, triazinyl, thiadiazolyl, oxazolyl, isoxazolyl, triazolyl, imidazolyl, thiophene-2-yl and thiophen-3-yl, 1-methyl-1 H-pyrazol-3-yl, wherein each heteroaromatic ring may be optionally substituted with 1-3 R20, R20 is halogen, nitro, C-pCg alkyl, C.|-Cg alkoxy. 6. The compound of the formula I according to Claim 1 wherein R3 is H; R4 is H, R21 is (-CHR22)mR23, m is 1, R22 is CrC6 alkyl, phenyl optionally substituted with 1-5 R20, R23 is, naphthyl, phenyl optionally substituted with 1-5 R20, R20 is halogen, nitro, C-j-Cg alkyl, C-pCg alkoxy, phenoxy, phenyl wherein each phenoxy, phenyl may be optionally substituted with 1-3 substitutents independently selected from R31, R31 is halogen, C1-C6 alkyl, CrC6 haloalkyl, benzyl, pyridyl. 7. The compound of the formula I according to Claim 1 wherein R3 is H; R4 is H, R21 is (-CHR22)mR23, m is 1, R22 is H, R23 is naphthlyl, benzo[1,3]dioxolyl, phenyl optionally substituted with 1-5 R20, R20 is halogen, cyano, nitro, amino, CrC6 alkoxyalkoxy, CrC6 alkyl, CrC6 haloalkyl, CrC6 hydroxyalkyl, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C6 alkenyl, hydroxyl, CrC6 alkoxy, CrC6 haloalkoxy, CrC6 alkylthio, CrC6 haloalkylthio, CrC6 alkylsulfonyl,
CrC6 alkylamino, benzyloxy, phenoxy, wherein each benzyloxy, phenoxy, may be optionally substituted with 1-3 substitutents independently selected from R31, R31 is halogen, CrC6 alkyl, CrC6 alkoxy. 8. The compound of the formula I according to Claim 1 wherein R3 is H; R4 is H, R21 is (-CHR22)mR23, m is 1, R22 is -CH3, -CH2CH3, -CH2CH2CH3, benzyl, 4-fluoro-phenyl, R23 is phenyl, 4-fluoro-phenyl, p-tolyl. 9. The compound of the formula I according to Claim 1 wherein R3 is H; R4 is H, R21 is (-CHR22)mR23, m is 1, R22 is H, R23 is phenyl, p-tolyl, 4-fluoro-phenyl, 4-methoxy-phenyl, 3-methoxy-phenyl, thiophen-2-yl, thiophen-3-yl, 3-fluor-ophenyl, 3-bromo-phenyl, benzothiophen-2-yl, 2,4,6-trimethyl-phenyl, 1-ethyl-2-methoxy-phenyl, 3-benzonitrile, 3-fluoro-4-methoxy-phenyl. 10. The compound of the formula I according to claim 1 selected from the compounds
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11. A composition for the control of afungal pathogen including the compound of any of Claims 1 to 10 and a phytologically acceptable carrier material. 12. The composition of Claim 11 wherein the fungal pathogen is one Apple Scab (Venturia inaequalis), Speckled Leaf Blotch of Wheat (Septoria tritici), Leaf spot of sugarbeets (Cercospora beticola), Leaf Spot of peanut (Cercospora arachidicola), and Black Sigatoka (Mycosphaerella fijiensis), 13. A method for the control and prevention of fungal attack on a plant, the method including the steps of: applying a fungicidally effective amount of at least one of the compounds of any of Claims 1 to 10 to at least one of the plant, an area adjacent to the plant, soil adapted to support growth of the plant, a root of the plant, foliage of the plant, and a seed adapted to produce at least one of the plant and another plant.
14. Use of a compound of formula I wherein R1 is -N(R3)R4;
R2 is -OR21; R3 is: H; R4 is: H; R8 is independently C^Cg alkyl, C^Cg haloalkyl, amino, C^Cg alkylamino, C2-C6 dialkylamino, phenyl optionally substituted with 1-3 R30, or a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11; R11 is independently halogen, C^Cg alkyl, CrC6 haloalkyl, C^Cg alkoxy, C^Cg haloalkoxy, Cr C6 alkylthio, CrC6 haloalkylthio, amino, C^Cg alkylamino, C2-C6 dialkylamino, C2-C6 alkoxycarbonyl, or C2-C6 alkylcarbonyl; R20 is independently halogen, cyano, nitro, amino, C^Cg alkoxyalkoxy, C^Cg alkyl, C^Cg haloalkyl, C^Cg hydroxy-alkyl, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, hydroxyl, CrCg alkoxy, CrC6 haloalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 haloalkynyloxy, C^Cg alkylthio, C^Cg haloalkylthio, C^Cg alkylsulfonyl, C^Cg haloalkylsulfonyl, C2-C6 alkenylthio, C2-C6 haloalkenylthio, C2-C6 haloalkenylsulfonyl, C3-C6 alkynylthio, C3-C6 alkynylsulfonyl, C3-C6 haloalkynylsulfo-nyl, C^Cg alkylamino, C2-C8 dialkylamino, C3-C8 dialkylaminocarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C3-Cgtrialkylsilyl, 2-[(E)-methoxyimino]-N-methyl-acetamidyl, phenyl, benzyl, benzyloxy, phenoxy,ora5-or6-mem-bered heteroaromatic ring wherein each phenyl, benzyl, benzyloxy, phenoxy, or 5- or 6- membered heteroaromatic ring may be optionally substituted with 1-3 substitutents independently selected from R31; R21 is: alkyl; C^Cg haloalkyl; C2-C4 alkenyl; C2-C4 haloalkenyl; C3-C4 alkynyl; C3-C4 haloalkynyl; phenyl, naphthyl, or tetrahydroquinolinyl each optionally substituted with 1-3 R20; -(CHR22)mR23; -(CHR24)mC(0)0R25; -(CHR24)mC(0)R26; -(CHR24)mC(0)N(R27)R28; -(CHR24)mOR29; -(CHR24)mSR29 -(CHR24)mN(R27)R28; -C(=0)R32; -N=C(R32)(R36); -NR25C(=0)0R25 -Si(R8)3; -S02R33; C2-C6 alkoxy carbonyl; C2-C6 alkylaminocarbonyl; C2-C6 alkylcarbonyl; sugars selected from the group consisting of beta-D-glucose-tetraacetate, rhamnose, fructose, and pentose; or a 5- or 6- membered heteroaromatic ring selected from the group consisting of furanyl, pyridinyl, pyridinyl-N-oxide, pyrimidinyl, pyridazinyl, pyrazinyl, pyrazolyl, thiazolyl, triazinyl, thiadiazolyl, oxazolyl, triazolylorisoxazolyl wherein each 5- or 6- member heteroaromatic ring may be optionally substituted with 1-5 R20; R22 is independently: H; halogen; cyano; nitro; C^Cg alkyl; C.|-Cg haloalkyl; phenyl or benzyl optionally substituted with 1-3 R20; C^Cg hydroxyalkyl; C2-C6 alkoxylalkyl; C3-C6 haloalkynyl; C2-C6 alkenyl; C2-C6 haloalkenyl; C3-C6 alkynyl; C^Cg alkoxy; C-pCg haloalkoxy; C-pCg alkylthio; C-pCg alkylamino; C2-C8 dialkylamino; C3-C6 cycloalkylamino; C4-C6 (alkyl)cycloalkylamino; C2-C6 alkylcarbonyl; C2-C6 alkoxycarbonyl; C2-C6 alkylaminocarbonyl; C3-C8 dialkylaminocarbonyl; C3-C6 trialkylsilyl; ring-fused heteroaromatic rings selected from the group consisting of benzothiophenyl, quinolinyl, isoquinolinyl, thieno[2,3-b]pyridyl, 1-methyl-1 H-thieno[2,3-c]pyrazolyl, and benzoimidazolyl, wherein each of the rings may be further substituted with 1 -3 R20; or a 5- or 6- membered heteroaromatic ring selected from the group consisting offuranyl, pyridinyl, pyridinyl-N-oxide, pyrimidinyl, pyridazinyl, pyrazinyl, thiazolyl, triazinyl, thiadiazolyl, oxazolyl, isoxazolyl, triazolyl and thienyl; R23 is: H; halogen; C^Cg alkyl; C^Cg haloalkyl; C2-C6 dialkylamino; phenyl optionally substituted with 1-5 R20; ring-fused heteroaromatic rings selected from the group consisting of benzothiophenyl, quinolinyl, isoquinolinyl, thieno[2,3-b]pyridyl, 1 -methyl-1 H-thieno[2,3-c]pyrazolyl, benzofuranyl and benzoimidazolyl, 2,3-dihydro-ben-zofuran-2-yl, 4-methyl-4H-thieno[3,2-b]pyrrol-5-yl, 1-methyl-1H-indol-5-yl, imidazo[1,2-a]pyridin-2-yl, imida-zo[2,1-b]thiazol-6-yl, benzothiazol-2-yl, benzo[b]thiophen-7-yl, and 1-methyl-1 H-indazol-3-yl, wherein each of the rings may be further substituted with 1-3 R20; naphthyl; benzo[1,3]dioxolyl; pyrrolidinonyl; oxetanyl; C^Cg alkylthio optionally substituted with 1-5 R20; a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11; or a 5- or 6- membered heteroaromatic ring selected from the group consisting offuranyl, pyridinyl, pyridinyl-N-oxide, pyrimidinyl, pyridazinyl, pyrazinyl, pyrazolyl, thiazolyl, triazinyl, thiadiazolyl, oxazolyl, isoxazolyl, triazolyl, imidazolyl, thiophene-2-yl and thiophen-3-yl wherein each heteroaromatic ring may be optionally substituted with 1-3 R20; R24 is H, CrC6 alkyl, C.|-Cg alkoxy, benzyl, or phenyl wherein each of the benzyl or phenyl may be optionally substituted with 1-3 R20; R25 is H, CrC6 alkyl, phenyl or benzyl optionally substituted with 1-3 R20; RZ6 is: H; C-|-Cg alkyl;
CrC6 alkoxy; phenyl optionally substituted with 1-3 R20; or a 5- or 6 membered heteroaromatic ring selected from the group consisting offuranyl, pyridinyl, pyridinyl-N-oxide, pyrimidinyl, pyridazinyl, pyrazinyl, thiazolyl, triazinyl, thiadiazolyl, oxazolyl, triazolyl and isoxazolyl; R27 and R28 are independently: H; , C^Cg alkyl; benzyl or phenyl wherein each of the benzyl or phenyl may be optionally substituted with 1-3 R20; or a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11; R29 is: H; C.|-C6 alkyl; C.|-Cg haloalkyl; C^Cg alkoxyalkyl; C2-C6 alkylcarbonyl; benzyl or phenyl wherein each of the benzyl or phenyl may be optionally substituted with 1-3 R20; or a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11; R30 is independently halogen, cyano, nitro, C^Cg alkyl, C^Cg haloalkyl, C^Cg hydroxyalkyl, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, hydroxyl, C^Cg alkoxy, C^Cg haloalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 haloalkynyloxy, C^Cg alkylthio, CrC6 alkylsulfonyl, CrC6 haloalkylsulfonyl, C2-C6 alkenylthio, C2-C6 haloalkenylthio, C2-C6 haloalkenylsulfonyl, C3-C6 alkynylthio, C3-C6 alkynylsulfonyl, C3-C6 haloalkynylsulfonyl, C^Cg alkylamino, C2-C8 dialkylamino, C3-C8 dialkylaminocarbonyl, C3-C6 trialkylsilyl, thiazolyl, phenyl, pyrimidinyl, orpyridyl, wherein the thiazolyl, phenyl, pyridyl, or pyrimidinyl may be optionally substituted with 1-3 R20; R31 is independently halogen, cyano, nitro, C^Cg alkyl, C^Cg haloalkyl, C^Cg hydroxyalkyl, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, hydroxyl, C-j-Cg alkoxy, C.|-Cg haloalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 haloalkynyloxy, C-pCg alkylthio, CrC6 alkylsulfonyl, CrC6 haloalkylsulfonyl, C2-C6 alkenylthio, C2-C6 haloalkenylthio, C2-C6 haloalkenylsulfonyl, C3-C6 alkynylthio, C3-C6 alkynylsulfonyl, C3-C6 haloalkynylsulfonyl, C-j-Cg alkylamino, C2-C8 dialkylamino, C3-C8 dialkylaminocarbonyl, or C3-C6 trialkylsilyl; R32 is independently:
CrC6 alkyl, C1-C6 haloalkyl, CrC6 hydroxyalkyl, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, hydroxyl, C^Cg alkoxy, C-pCg haloalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 haloalkynyloxy, C-j-Cg alkylthio, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C2-C6 alkenylthio, C2-C6 haloalkenylthio, C2-C6 haloalkenylsulfonyl, C3-C6 alkynylthio, C3-C6 alkynylsulfonyl, C3-C6 haloalkynylsulfonyl, 0.,-Cg alkylamino, C2-C8 dialkylamino, C3-C8 dialkylaminocarbonyl, C3-C6 trialkylsilyl; phenyl wherein the phenyl ring may be optionally substituted with 1-3 R20; or a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11; R33 is independently: C^Cg alkyl, C1-C6 haloalkyl, phenyl or thienyl optionally substituted with 1-3 R20; or a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11; R34 is: C^Cg alkyl, C-pCg haloalkyl, C2-C6 alkoxyalkyl, C-pCg alkylamino; or a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11; R35 is: C^Cg alkyl, C2-C6 alkylcarbonyl; or a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11; R36 is H, cyano, 0Γ06 alkyl, C^Cg alkoxy, benzyl, or phenyl wherein each of the benzyl or phenyl may be optionally substituted with 1-3 R20; alternatively R32 and R36 may be taken together to form: a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11; and R37 is independently: H, halogen, or phenyl optionally substituted with 1-5 R20; C^Cg alkyl, C^Cg haloalkyl, hydroxyl, C^Cg alkoxy, orC^Cg haloalkoxy; or a 5- or 6- membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R11, for the protection of a plant against attack by a fungal pathogen.
Patentansprüche
1. Verbindung der Formel I
wobei R1 -N(R3)R4 ist; R2-OR21 ist; R3 H ist; R4 H ist; R8 unabhängig C1-C6-Alkyl, C^Cg-Halogenalkyl, Amino, C^Cg-Akylamino, C2-C6-Dialkylamino, Phenyl, welches gegebenenfalls mit 1 -3 R30 substituiert ist, oder ein 5- oder 6-gliedriger gesättigter oder ungesättigter Ring, welcher 1-3 Heteroatome enthält, wobei jeder Ring gegebenenfalls mit 1-3 R11 substituiert sein kann, ist; R11 unabhängig Halogen, C^Cg-Alkyl, C^-Cg-Halogenalkyl, C^Cg-Alkoxy, C^Cg-Halogenalkoxy, C^Cg-AI-kylthio, C^Cg-Halogenalkylthio, Amino, C-pCg-Alkylamino, C2-C6-Dialkylamino, C2-C6-Alkoxycarbonyl oder C2-C6-Alkylcarbonyl ist; R20 unabhängig Halogen, Cyano, Nitro, Amino, C1-C6-Alkoxyalkoxy, C^Cg-Alkyl, C1-C6-Halogenalkyl, C1-C6-Hydroxyalkyl, C2-C6-Alkoxyalkyl, C2-C6-Halogenalkoxyalkyl, C2-C6-Alkenyl, C2-C6-Halogenalkenyl, C3-C6-Alkinyl, C3-C6-Halogenalkinyl, Hydroxyl, C^Cg-Alkoxy, C^Cg-Halogenalkoxy, C2-C6-Alkenyloxy, C2-C6-Halogenalkenyloxy, C3-C6-Alkinyloxy, C3-C6-Halogenalkinyloxy, C^Cg-Alkylthio, C^Cg-Halogenal-kylthio, C^Cg-Alkylsulfonyl, C^Cg-Halogenalkylsulfonyl, C2-C6-Alkenylthio, C2-C6-Halogenalkenylthio, C2-C6-Halogenalkenylsulfonyl, C3-C6-Alkinylthio, C3-C6-Alkinylsulfonyl, C3-C6-Halogenalkinylsulfonyl, C-i-Cg-Alkylamino, C2-C8-Dialkylamino, C3-C8-Dialkylaminocarbonyl, C2-C6-Alkoxycarbonyl, C2-C6-Alkyl carbonyl, C3-C6-Trialkylsilyl, 2-[(E)-Methoxyimino]-N-methyl-acetamidyl, Phenyl, Benzyl, Benzyloxy, Phenoxy oder ein 5- oder 6-gliedriger heteroaromatischer Ring ist, wobei jedes Phenyl, Benzyl, Benzyloxy, Phenoxy oder jeder 5- oder 6-gliedrige heteroaromatische Ring gegebenenfalls mit 1-3 Substitutenten, die unabhängig aus R31 ausgewählt sind, substituiert sein kann; R21: C-pC-14-Alkyl; C1-C6-Halogenalkyl; C2-C4-Alkenyl; C2-C4-Halogenalkenyl; C3-C4-Alkinyl; C3-C4-Halogenalkinyl;
Phenyl, Naphthyl oderTetrahydrochinolinyl, welches jeweils gegebenenfalls mit 1-3 R20 substituiert ist; -(CHR22)mR23; -(CHR24)mC(0)0R25; -(CH R24)mC(0) R26 ; -(CHR24)mC(0)N(R27)R28; -(CHR24)mOR29; -(CHR24)mSR29; -(CHR24)mN(R27)R28; -C(=0)R32; -N=C(R32)(R36); -NR25C(=0)0R25; -Si(R8)3; -S02R33; C2-C6-Alkoxycarbo ny I ; C2-C6-Alkylaminocarbonyl; C2-C6-Alkylcarbonyl;
Zucker, ausgewählt aus der Gruppe bestehend aus beta-D-Glucosetetraacetat, Rhamnose, Fructose und Pentose; oder ein 5- oder 6-gliedriger heteroaromatischer Ring, ausgewählt aus der Gruppe bestehend aus Furanyl, Pyridinyl, Pyridinyl-N-oxid, Pyrimidinyl, Pyridazinyl, Pyrazinyl, Pyrazolyl, Thiazolyl, Triazinyl, Thiadiazolyl, Oxazolyl, Triazolyl oder Isoxazolyl, wobei jeder 5- oder 6-gliedrige heteroaromatische Ring gegebenenfalls mit 1-5 R20 substituiert sein kann, ist, wobei m eine ganze Zahl von 1-3 ist; R22 unabhängig: H;
Halogen;
Cyano;
Nitro;
Ci-Cg-Alkyl; C^Cg-Halogenalkyl;
Phenyl oder Benzyl, welches gegebenenfalls mit 1-3 R20 substituiert ist; C-pCg-Hydroxyalkyl; C2-C6-Alkoxylalkyl; C3-C6-Halogenalkinyl; C2-C6-Alkenyl; C2-C6-Halogenalkenyl; C3-C6-Alkinyl; C^Cg-Alkoxy; C1-C6-Halogenalkoxy; C^Cg-Alkylthio; C^Cg-Alkylamino; C2-C8-Dialkylamino; C3-Cg-Cycloalkylamino; C4-C6-( AI ky Ijcycloa Iky la m i no ; C2-C6-Alky Icarbonyl ; C2-C6-Alkoxycarbonyl; C2-C6-Alkylaminocarbonyl; C3-C8-Dialkylaminocarbonyl; C3-C6-Trialkylsilyl; heteroaromatische Ringe mit fusionierten Ringen, ausgewählt aus der Gruppe bestehend aus Benzothio-phenyl, Chinolinyl, Isochinolinyl, Thieno[2,3-b]pyridyl, 1-Methyl-1H-thieno[2,3-c]pyrazolyl und Benzoimida-zolyl, wobei jeder der Ringe weiterhin mit 1-3 R20 substituiert sein kann; oder ein 5- oder 6-gliedriger heteroaromatischer Ring, ausgewählt aus der Gruppe bestehend aus Furanyl, Pyridinyl, Pyridinyl-N-oxid, Pyrimidinyl, Pyridazinyl, Pyrazinyl, Thiazolyl, Triazinyl, Thiadiazolyl, Oxazolyl, Isoxazolyl, Triazolyl und Thienyl, ist; R23; H;
Halogen; C-j-Cg-Alkyl; C^Cg-Halogenalkyl; C2-C6-Dialkylamino;
Phenyl, welches gegebenenfalls mit 1-5 R20 substituiert ist; heteroaromatische Ringe mit fusionierten Ringen, ausgewählt aus der Gruppe bestehend aus Benzothiophenyl, Chinolinyl, Isochinolinyl, Thieno[2,3-b]pyridyl, 1-Methyl-1 H-thieno[2,3-c]pyrazolyl, Benzofuranyl und Benzoimidazolyl, 2,3-Dihydro-benzofuran-2-yl, 4-Methyl-4H-thieno[3,2-b]pyrrol-5-yl, 1-Methyl-1 H-indol-5-yl, lmidazo[1,2-a]pyridin-2-yl, lmidazo[2,1-b]thiazol-6-yl, Benzothiazol-2-yl, Benzo[b]thiophen-7-yl und 1 -Methyl-1 H-indazol-3-yl, wobei jeder der Ringe weiterhin mit 1-3 R20 substituiert sein kann;
Naphthyl;
Benzo[1,3]dioxolyl;
Pyrrolidinonyl;
Oxetanyl; C^Cg-Alkylthio, welches gegebenenfalls mit 1-5 R20 substituiert ist; ein 5- oder 6-gliedriger gesättigter oder ungesättigter Ring, welcher 1-3 Heteroatome enthält, wobei jeder Ring gegebenenfalls mit 1-3 R11 substituiert sein kann; oder ein 5- oder 6-gliedriger heteroaromatischer Ring, ausgewählt aus der Gruppe bestehend aus Furanyl, Pyridinyl, Pyridinyl-N-oxid, Pyrimidinyl, Pyridazinyl, Pyrazinyl, Pyrazolyl, Thiazolyl, Triazinyl, Thiadiazolyl, Oxazolyl, Isoxazolyl, Triazolyl, Imidazolyl, Thiophen-2-yl und Thiophen-3-yl, wobei jeder heteroaromatische Ring gegebenenfalls mit 1-3 R20 substituiert sein kann, ist; R24 H, C^Cg-Alkyl, C^Cg-Alkoxy, Benzyl oder Phenyl ist, wobei jedes Benzyl oder Phenyl gegebenenfalls mit 1-3 R20 substituiert sein kann; R25 H, C^Cg-Alkyl, gegebenenfalls mit 1-3 R20 substituiertes Phenyl oder Benzyl, ist; R26: H; C1-Cg-Alkyl; C^Cg-Alkoxy; gegebenenfalls mit 1-3 R20 substituiertes Phenyl; oder ein 5- oder 6-gliedriger heteroaromatischer Ring, ausgewählt aus der Gruppe bestehend aus Furanyl, Pyridinyl, Pyridinyl-N-oxid, Pyrimidinyl, Pyridazinyl, Pyrazinyl, Thiazolyl, Triazinyl, Thiadiazolyl, Oxazolyl, Triazolyl und Isoxazolyl ist; R27 und R28 unabhängig: H; C-|-Cg-Alkyl;
Benzyl oder Phenyl, wobei jedes Benzyl oder Phenyl gegebenenfalls mit 1-3 R20 substituiert sein kann; oder ein 5- oder 6-gliedriger gesättigter oder ungesättigter Ring, welcher 1-3 Heteroatome enthält, wobei jeder Ring gegebenenfalls mit 1-3 R11 substituiert sein kann, sind; R28: H; C-|-Cg-Alkyl; C-j-Cg-Halogenalkyl; C1-Cg-Al koxya I ky I ; C2-C6-Alkylcarbonyl;
Benzyl oder Phenyl, wobei jedes Benzyl oder Phenyl gegebenenfalls mit 1-3 R20 substituiert sein kann; oder ein 5- oder 6-gliedriger gesättigter oder ungesättigter Ring, welcher 1-3 Heteroatome enthält, wobei jeder Ring gegebenenfalls mit 1-3 R11 substituiert sein kann, ist; R30 unabhängig Halogen, Cyano, Nitro, C-pCg-Alkyl, C^Cg-Halogenalkyl, C1-C6-Hydroxyalkyl, C2-C6-Alkoxy-alkyl, C2-C6-Halogenalkoxyalkyl, C2-C6-Alkenyl, C2-C6-Halogenalkenyl, C3-C6-Alkinyi, C3-C6-Halogenalkinyl, Hydroxyl, C1-C6-Alkoxy, C-j-Cg-Halogenalkoxy, C2-C6-Alkenyloxy, C2-C6-Halogenalkenyloxy, C3-C6-Alkinyloxy, C3-C6-Halogenalkinyloxy, C-pCg-Alkylthio, C-pCg-Alkylsulfonyl, C-pCg-Halogenalkylsulfonyl, C2-C6-Alkenylthio, C2-C6-Halogenalkenylthio, C2-C6-Halogenalkenylsulfonyl, C3-C6-Alkinylthio, C3-C6-Alkinylsulfonyl, C3-C6-Ha-logenalkinylsulfonyl, C^Cg-Alkylamino, C2-C8-Dialkylamino, C3-C8-Dialkylaminocarbonyl, C3-C6-Trialkylsilyl, Thiazolyl, Phenyl, Pyrimidinyl oder Pyridyl ist, wobei das Thiazolyl, Phenyl, Pyridyl oder Pyrimidinyl gegebenenfalls mit 1-3 R20 substituiert sein kann; R31 unabhängig Halogen, Cyano, Nitro, C^Cg-Alkyl, C-j-Cg-Halogenalkyl, C1-C6-Hydroxyalkyl, C2-C6-Alkoxy-alkyl, C2-C6-Halogenalkoxyalkyl, C2-C6-Alkenyl, C2-C6-Halogenalkenyl, C3-C6-Alkinyi, C3-C6-Halogenalkinyl, Hydroxyl, C-pCg-Alkoxy, C-pCg-Halogenalkoxy, C2-C6-Alkenyloxy, C2-C6-Halogenalkenyloxy, C3-C6-Alkinyloxy, C3-C6-Halogenalkinyloxy, C-pCg-Alkylthio, C.|-Cg-Alkylsulfonyl, C-pCg-Halogenalkylsulfonyl, C2-C6-Alkenylthio, C2-C6-Halogenalkenylthio, C2-Cg-Halogenalkenylsulfonyl, C3-C6-Alkinylthio, C3-C6-Alkinylsulfonyl, C3-C6-Ha-logenalkinylsulfonyl, C^Cg-Alkylamino, C2-C8-Dialkylamino, C3-C8-Dialkylaminocarbonyl oder C3-C6-Trialkyl-silyl ist; R32 unabhängig: C^Cg-Alkyl, C^Cg-Halogenalkyl, C1-C6-Hydroxyalkyl, C2-C6-Alkoxyalkyl, C2-C6-Halogenalkoxyalkyl, C2-C6-Alkenyl, C2-C6-Halogenalkenyl, C3-C6-Alkinyl, C3-C6-Halogenalkinyl, Hydroxyl, C-pCg-Alkoxy, C^Cg-Halogenalkoxy, C2-C6-Alkenyloxy, C2-C6-Halogenalkenyloxy, C3-C6-Alkinyloxy, C3-C6-Halogenal-kinyloxy, C^Cg-Alkylthio, C^Cg-Alkylsulfonyl, C1-C6-Halogenalkylsulfonyl, C2-C6-Alkenylthio, C2-C6-Ha-logenalkenylthio, C2-C6-Halogenalkenylsulfonyl, C3-C6-Alkinylthio, C3-C6-Alkinylsulfonyl, C3-C6-Halo-genalkinylsulfonyl, C^Cg-Alkylamino, C2-C8-Dialkylamino, C3-C8-Dialkylaminocarbonyl, C3-C6-Trialkylsi- lyi;
Phenyl, wobei der Phenylring gegebenenfalls mit 1-3 R20 substituiert sein kann; oder ein 5- oder 6-gliedriger gesättigter oder ungesättigter Ring, welcher 1-3 Heteroatome enthält, wobei jeder
Ring gegebenenfalls mit 1-3 R11 substituiert sein kann, ist; R33 unabhängig: C1-Cg-Alkyl, C^Cg-Halogenalkyl, gegebenenfalls mit 1-3 R20 substituiertes Phenyl oder Thienyl; oder ein 5- oder 6-gliedriger gesättigter oder ungesättigter Ring, welcher 1-3 Heteroatome enthält, wobei jeder Ring gegebenenfalls mit 1-3 R11 substituiert sein kann, ist; r34: C^Cg-Alkyl, C1-Cg-Halogenalkyl, C2-C6-Alkoxyalkyl, C1-C6-Alkylamino; oder ein 5- oder 6-gliedriger gesättigter oder ungesättigter Ring, welcher 1-3 Heteroatome enthält, wobei jeder Ring gegebenenfalls mit 1-3 R11 substituiert sein kann, ist; R35: C^Cg-Alkyl, C2-C6-Alkylcarbonyl; oder ein 5- oder 6-gliedriger gesättigter oder ungesättigter Ring, welcher 1-3 Heteroatome enthält, wobei jeder Ring gegebenenfalls mit 1-3 R11 substituiert sein kann, ist; R36 H, Cyano, CrC6-Alkyl, CrC6-Alkoxy, Benzyl oder Phenyl ist, wobei jedes Benzyl oder Phenyl gegebenenfalls mit 1-3 R20 substituiert sein kann; alternativ können R32 und R36 zusammengenommen sein, um: einen 5- oder 6-gliedrigen gesättigten oder ungesättigten Ring, welcher 1-3 Heteroatome enthält, wobei jeder Ring gegebenenfalls mit 1-3 R11 substituiert sein kann, zu bilden; und R37 unabhängig: H, Halogen oder gegebenenfalls mit 1-5 R20 substituiertes Phenyl; C^Cg-Alkyl, C^Cg-Halogenalkyl, Hydroxyl, C^Cg-Alkoxy oder C^Cg-Halogenalkoxy; oder ein 5- oder 6-gliedriger gesättigter oder ungesättigter Ring, welcher 1-3 Heteroatome enthält, wobei jeder
Ring gegebenenfalls mit 1-3 R11 substituiert sein kann, ist; mit der Maßgabe, dass die Verbindung nicht 4-Amino-5-fluor-2-tri-C1-C7-alkyl-silyloxypyrimidin, 2-Ethoxy-4-amino-5-fluorpyrimidin oder 2-Methoxy-4-amino-5-fluorpyrimidin ist. 2. Verbindung der Formel I gemäß Anspruch 1, wobei R3 H ist; R4 H ist, R21 - C(=0)R32, -N=C(R32)(R36), -S02R33, NR25C(=0)0R25, C1-C6-Alkyl, CrC6-Alkoxy ist, R25 H, CrC6-Alkyl ist, R32 C1-C6-Alkyl, Phenyl, wobei das Phenyl gegebenenfalls mit 1-3 R20 substituiert sein kann, ist, R33 C^Cg-Alkyl, gegebenenfalls mit 1-3 R20 substituiertes Phenyl oder Thienyl ist, R36 Cyano, C1-C6-Alkyl, Phenyl, wobei das Phenyl gegebenenfalls mit 1-3 R20 substituiert sein kann, ist und R20 Halogen, C^Cg-Alkyl, C^Cg-Alkoxy ist. 3. Verbindung der Formel I gemäß Anspruch 1 .wobei R3H ist; R4H ist, R21 (-CHR22)mR23ist, m 1 ist, R22 H, C-j-C^Alkyl, Phenyl ist, R23 ein heteroaromatischer Ringe mit fusionierten Ringen, ausgewählt aus der Gruppe bestehend aus Benzothiophenyl, Chinolinyl, Isochinolinyl, Thieno[2,3-b]pyridyl, 1-Methyl-1 H-thieno[2,3-c]pyrazolyl, Benzofuranyl und Benzoimidazolyl, 2,3-Dihydro-benzofuran-2-yl, 4-Methyl-4H-thieno[3,2-b]pyrrol-5-yl, 1-Methyl-1H-indol-5-yl, lmidazo[1,2-a]pyridin-2-yl, lmidazo[2,1-b]thiazol-6-yl, Benzothiazol-2-yl, Benzo[b]thiophen-7-yl, 1-Methyl-1H-inda-zol-3-yl, wobei jeder der Ringe gegebenenfalls weiterhin mit 1-3 R20 substituiert sein kann, ist, R20 Halogen, C-pCg-AI-kyl, Ci-Cg-Alkoxy ist. 4. Verbindung der Formel I gemäß Anspruch 1, wobei R3 H ist; R4 H ist, R21 (-CHR22)mR23 ist, m 1 ist, R22 H ist, R23 ein 5- oder 6-gliedriger gesättigter oder ungesättigter Ring, welcher 1-3 Heteroatome enthält, wobei jeder Ring gegebenenfalls mit 1-3 R11 substituiert sein kann, ist. 5. Verbindung der Formel I gemäß Anspruch 1, wobei R3 H ist; R4 H ist, R21 (-CHR22)mR23 ist, m 1 ist, R22 H ist, R23 ein 5- oder 6-gliedriger heteroaromatischer Ring, ausgewählt aus der Gruppe bestehend aus Furanyl, Pyridinyl, Pyridinyl-N-oxid, Pyrimidinyl, Pyridazinyl, Pyrazinyl, Pyrazolyl, Thiazolyl, Triazinyl, Thiadiazolyl, Oxazolyl, Isoxazolyl, Triazolyl, Imidazolyl, Thiophen-2-yl und Thiophen-3-yl, 1-Methyl-1 H-pyrazol-3-yl, wobei jeder heteroaromatische Ring gegebenenfalls mit 1-3 R20 substituiert sein kann, ist, R20 Halogen, Nitro, C^Cg-Alkyl, C^Cg-Alkoxy ist. 6. Verbindung der Formel I gemäß Anspruch 1, wobei R3 H ist; R4 H ist, R21 (-CHR22)mR23 ist, m 1 ist, R22 C-pCg-Alkyl, gegebenenfalls mit 1-5 R20 substituiertes Phenyl ist, R23 Naphthyl, gegebenenfalls mit 1-5 R20 substituiertes Phenyl ist, R20 Halogen, Nitro, C1-C6-Alkyl, C1-C6-Alkoxy, Phenoxy, Phenyl, wobei jedes Phenoxy, Phenyl gegebenenfalls mit 1-3 Substitutenten, die unabhängig aus R31 ausgewähltsind, substituiert sein kann, ist, R31 Halogen, C-j-Cg-Alkyl, C^Cg-Halogenalkyl, Benzyl, Pyridyl ist. 7. Verbindung der Formel I gemäß Anspruch 1, wobei R3 H ist; R4 H ist, R21 (-CHR22)mR23 ist, m 1 ist, R22 H ist, R23 Naphthyl, Benzo[1.3]dioxolyl, gegebenenfalls mit 1-5 R20substituiertes Phenyl ist, R20 Halogen, Cyano, Nitro, Amino, C-|-Cg-Alkoxyalkoxy, C^Cg-Alkyl, C-pCg-Halogenalkyl, C^Cg-Hydroxyalkyl, C2-C6-Alkoxyalkyl, C2-C6-Halogenalk-oxyalkyl, C2-C6-Alkenyl, Hydroxyl, C^Cg-Alkoxy, C^Cg-Halogenalkoxy, C^Cg-Alkylthio, C^Cg-Halogenalkylthio, C^Cg-Alkylsulfonyl, C^Cg-Alkylamino, Benzyloxy, Phenoxy, wobei jedes Benzyloxy, Phenoxy gegebenenfalls mit 1-3 Substitutenten, die unabhängig aus R31 ausgewähltsind, substituiert sein kann, ist, R31 Halogen, C^Cg-Alkyl, C^Cg-Alkoxy ist. 8. Verbindung der Formel I gemäß Anspruch 1, wobei R3 H ist; R4 H ist, R21 (-CHR22)mR23 ist, m 1 ist, R22 -CH3, -CH2CH3, -CH2CH2CH3, Benzyl, 4-Fluor-phenyl ist, R23 Phenyl, 4-Fluor-phenyl, p-Tolyl ist. 9. Verbindung der Formel I gemäß Anspruch 1, wobei R3 H ist; R4 H ist, R21 (-CHR22)mR23 ist, m 1 ist, R22 H ist, R23 Phenyl, p-Tolyl, 4-Fluor-phenyl, 4-Methoxy-phenyl, 3-Methoxy-phenyl, Thiophen-2-yl, Thiophen-3-yl, 3-Fluor-phe-nyl, 3-Brom-phenyl, Benzothiophen-2-yl, 2,4,6-Trimethyl-phenyl, 1-Ethyl-2-methoxy-phenyl, 3-Benzonitril, 3-Fluor-4-methoxy-phenyl ist. 10. Verbindung der Formel I gemäß Anspruch 1, ausgewählt aus den Verbindungen:
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11. Zusammensetzung zur Kontrolle eines pathogenen Pilzes, umfassend die Verbindung nach einem der Ansprüche 1 bis 10 und ein phythologisch verträgliches Trägermaterial. 12. Zusammensetzung nach Anspruch 11, wobei der pathogene Pilz einer ausgewählt aus Apfelschorf {Venturis ina-equalis), Blattdürre bei Weizen {Septoria tritici), amerikanischer Blattkrankheit bei Zuckerrüben (Cercospora beti-cola), amerikanischer Blattkrankheit bei Erdnüssen {Cercospora arachidicola) und schwarzen Blattmasern {Mycos-phaerella fijiensis) ist. 13. Verfahren zur Kontrolle und Prävention von Pilzbefall auf einer Pflanze, wobei das Verfahren die Schritte:
Aufbringen einer fungizid wirksamen Menge mindestens einer der Verbindungen nach einem der Ansprüche 1 bis 10 auf mindestens eines ausgewählt aus der Pflanze, einem an die Pflanze angrenzenden Bereich, Boden, der dazu geeignet ist, das Wachstum der Pflanze zu fördern, einer Wurzel der Pflanze, Blattwerk der Pflanze und einem Samen, der dazu geeignet ist, mindestens eines ausgewählt aus der Pflanze und einer anderen Pflanze zu bilden, umfasst. 14. Verwendung einer Verbindung der Formel I wobei
R1 -N(R3)R4 ist; R2 -OR21 ist; R3 H ist; R4 H ist; R8 unabhängig C-j-Cg-Alkyl, C1-C6-Halogenalkyl, Amino, C-j-Cg-Akylamino, C2-C6-Dialkylamino, Phenyl, welches gegebenenfalls mit 1 -3 R30 substituiert ist, oder ein 5- oder 6-gliedriger gesättigter oder ungesättigter Ring, welcher 1-3 Heteroatome enthält, wobei jeder Ring gegebenenfalls mit 1-3 R11 substituiert sein kann, ist; R11 unabhängig Halogen, C^Cg-Alkyl, C-pCg-Halogenalkyl, C^Cg-Alkoxy, C-pCg-Halogenalkoxy, C.|-Cg-Al-kylthio, C^Cg-Halogenalkylthio, Amino, C.|-Cg-Alkylamino, C2-C6-Dialkylamino, C2-C6-Alkoxycarbonyl oder C2-C6-Alkylcarbonyl ist; R20 unabhängig Halogen, Cyano, Nitro, Amino, CrC6-Alkoxyalkoxy, C1-C6-Alkyl, C1-C6-Halogenalkyl, C-i-Cg-Hydroxyalkyl, C2-Cg-Alkoxyalkyl, C2-Cg-Halogenalkoxyalkyl, C2-C6-Alkenyl, C2-C6-Halogenalkenyl, C3-Cg-Alkinyl, C3-C6-Halogenalkinyl, Hydroxyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy, C2-C6-Alkenyloxy, C2-C6-Halogenalkenyioxy, C3-C6-Alkinyloxy, C3-C6-Halogenalkinyloxy, C-pCg-Alkylthio, C.|-Cg-Halogenal-kylthio, C^Cg-Alkylsulfonyl, C-pCg-Halogenalkylsulfonyl, C2-C6-Alkenylthio, C2-C6-Halogenalkenylthio, C2-C6-Halogenalkenylsulfonyl, C3-C6-Alkinylthio, C3-C6-Alkinylsulfonyl, C3-C6-Halogenalkinylsulfonyl, C-|-Cg-Alkylamino, C2-C8-Dialkylamino, C3-C8-Dialkylaminocarbonyl, C2-C6-Alkoxycarbonyl, C2-C6-Alkylcarbo-nyl, C3-Cg-Trialkylsilyl, 2-[(E)-Methoxyimino]-N-methyl-acetamidyl, Phenyl, Benzyl, Benzyloxy, Phenoxy oder ein 5- oder 6-gliedriger heteroaromatischer Ring ist, wobei jedes Phenyl, Benzyl, Benzyloxy, Phenoxy oder jeder 5- oder 6-gliedrige heteroaromatische Ring gegebenenfalls mit 1-3 Substitutenten, die unabhängig aus R31 ausgewählt sind, substituiert sein kann; R21:
Ci-C14-Alkyl;
Ci-C6-Halogenalkyl; C2-C4-Alkenyl; C2-C4-Halogenalkenyl; C3-C4-Alkinyl; C3-C4-Halogenalkinyl;
Phenyl, Naphthyl oder Tetrahydrochinolinyl, welches jeweils gegebenenfalls mit 1-3 R20 substituiert ist; -(CHR22)mR23; -(CHR24)mC(0)0R25; -(CHR24)mC(0)R26; -(CHR24)mC(0)N(R27)R28; -(CHR24)mOR29; -(CHR24)mSR29; -(CHR24)mN(R27)R28; -C(=0)R32; -N=C(R32)(R36); -NR25C(=0)0R25; -Si(R8)3; -S02R33; C2-C6-Alkoxycarbo ny I ; C2-Cg-Alkylaminocarbonyl; C2-Cg-Alkylcarbonyl;
Zucker, ausgewählt aus der Gruppe bestehend aus beta-D-Glucosetetraacetat, Rhamnose, Fructose und Pentose; oder ein 5- oder 6-gliedriger heteroaromatischer Ring, ausgewählt aus der Gruppe bestehend aus Furanyl, Pyridinyl, Pyridinyl-N-oxid, Pyrimidinyl, Pyridazinyl, Pyrazinyl, Pyrazolyl, Thiazolyl, Triazinyl, Thiadiazolyl, Oxazolyl, Triazolyl oder Isoxazolyl, wobei jeder 5- oder 6-gliedrige heteroaromatische Ring gegebenenfalls mit 1-5 R20 substituiert sein kann, ist, R22 unabhängig: H;
Halogen;
Cyano;
Nitro; C-|-Cg-Alkyl; C^Cg-Halogenalkyl;
Phenyl oder Benzyl, welches gegebenenfalls mit 1-3 R20 substituiert ist; C^Cg-Hydroxyalkyl, C2-Cg-Alkoxylalkyl; C3-Cg-Halogenalkinyl; C2-C6-Alkenyl; C2-Cg-Halogenalkenyl; C3-C6-Alkinyl; C^Cg-Alkoxy-, C-|-Cg-Halogenalkoxy-, C1-C6-Alkylthio-, C^Cg-Alkylamino; C2-C8-Dialkylamino;
Cg-Cg-Cycloalkylamino; C4-C6-(AI kyl)cycloalky la m i no ; C2-C6-Alkylcarbonyl; C2-C6-Alkoxycarbo ny I ; C2-C6-Alkylaminocarbonyl;
Cg-Cg-Dialkylaminocarbonyl;
Cg-Cg-Tnalkylsilyl; heteroaromatische Ringe mit fusionierten Ringen, ausgewählt aus der Gruppe bestehend aus Benzothio-phenyl, Chinolinyl, Isochinolinyl, Thieno[2,3-b]pyridyl, 1 -Methyl-1 H-thieno[2,3-c]pyrazolyl und Benzoimida-zolyl, wobei jeder der Ringe weiterhin mit 1-3 R20 substituiert sein kann; oder ein 5- oder 6-gliedriger heteroaromatischer Ring, ausgewählt aus der Gruppe bestehend aus Furanyl, Pyridinyl, Pyridinyl-N-oxid, Pyrimidinyl, Pyridazinyl, Pyrazinyl, Thiazolyl, Triazinyl, Thiadiazolyl, Oxazolyl, Isoxazolyl, Triazolyl und Thienyl, ist; R23: H;
Halogen; C-j-Cg-Alkyl-, C1-Cg-Halogenalkyl; C2-C6-Dialkylamino;
Phenyl, welches gegebenenfalls mit 1-5 R20 substituiert ist; heteroaromatische Ringe mit fusionierten Ringen, ausgewählt aus der Gruppe bestehend aus Benzothiophenyl, Chinolinyl, Isochinolinyl, Thieno[2,3-b]pyridyl, 1-Methyl-1 H-thieno[2,3-c]pyrazolyl, Benzofuranyl und Benzoimidazolyl, 2,3-Dihydro-benzofuran-2-yl, 4-Methyl-4H-thieno[3,2-b]pyrrol-5-yl, 1-Methyl-1 H-indol-5-yl, lmidazo[1,2-a]pyridin-2-yl, lmidazo[2,1-b]thiazol-6-yl, Benzothiazol-2-yl, Benzo[b]thiophen-7-yl und 1-Methyl-1 H-indazol-3-yl, wobei jeder der Ringe weiterhin mit 1-3 R20 substituiert sein kann;
Naphthyl;
Benzo[1,3]dioxolyl;
Pyrrolidinonyl;
Oxetanyl; C-|-Cg-Alkylthio, welches gegebenenfalls mit 1-5 R20 substituiert ist; ein 5- oder 6-gliedriger gesättigter oder ungesättigter Ring, welcher 1-3 Heteroatome enthält, wobei jeder Ring gegebenenfalls mit 1-3 R11 substituiert sein kann; oder ein 5- oder 6-gliedriger heteroaromatischer Ring, ausgewählt aus der Gruppe bestehend aus Furanyl, Pyridinyl, Pyridinyl-N-oxid, Pyrimidinyl, Pyridazinyl, Pyrazinyl, Pyrazolyl, Thiazolyl, Triazinyl, Thiadiazolyl, Oxazolyl, Isoxazolyl, Triazolyl, Imidazolyl, Thiophen-2-yl und Thiophen-3-yl, wobei jeder heteroaromatische Ring gegebenenfalls mit 1-3 R20 substituiert sein kann, ist; R24 H, C^Cg-Alkyl, C^Cg-Alkoxy, Benzyl oder Phenyl ist, wobei jedes Benzyl oder Phenyl gegebenenfalls mit 1-3 R20 substituiert sein kann; R25 H, C^Cg-Alkyl, gegebenenfalls mit 1-3 R20 substituiertes Phenyl oder Benzyl, ist; R26: H; C1-C6-Alkyl; C^Cg-Alkoxy; gegebenenfalls mit 1-3 R20 substituiertes Phenyl; oder ein 5- oder 6-gliedriger heteroaromatischer Ring, ausgewählt aus der Gruppe bestehend aus Furanyl, Pyridinyl, Pyridinyl-N-oxid, Pyrimidinyl, Pyridazinyl, Pyrazinyl, Thiazolyl, Triazinyl, Thiadiazolyl, Oxazolyl, Triazolyl und Isoxazolyl ist; R27 und R28 unabhängig: H; C1-C6-Alkyl;
Benzyl oder Phenyl, wobei jedes Benzyl oder Phenyl gegebenenfalls mit 1-3 R20 substituiert sein kann; oder ein 5- oder 6-gliedriger gesättigter oder ungesättigter Ring, welcher 1-3 Heteroatome enthält, wobei jeder Ring gegebenenfalls mit 1-3 R11 substituiert sein kann, sind; R29: H;
Ci-Cg-Alkyl; C^Cg-Halogenalkyl; C^Cg-Alkoxyalkyl; C2-C6-Alkylcarbonyl;
Benzyl oder Phenyl, wobei jedes Benzyl oder Phenyl gegebenenfalls mit 1-3 R20 substituiert sein kann; oder ein 5- oder 6-gliedriger gesättigter oder ungesättigter Ring, welcher 1-3 Heteroatome enthält, wobei jeder Ring gegebenenfalls mit 1-3 R11 substituiert sein kann, ist; R30 unabhängig Halogen, Cyano, Nitro, C1-C6-Alkyl, C1-C6-Halogenalkyl, C1-C6-Hydroxyalkyl, C2-C6-Alkoxy-alkyl, C2-C6-Halogenalkoxyalkyl, C2-C6-Alkenyl, C2-C6-Halogenalkenyl, C3-C6-Alkinyi, C3-C6-Haiogenalkinyl, Hydroxyl, Ci-C6-Alkoxy, Ci-C6-Halogenalkoxy, C2-C6-Alkenyloxy, C2-C6-Halogenalkenyloxy, C3-C6-Alkinyloxy, C3-C6-Halogenalkinyloxy, Ci-C6-Alkylthio, C1-C6-Alkylsulfonyl, C1-C6-Halogenalkylsulfonyl, C2-C6-Alkenylthio, C2-C6-Halogenalkenylthio, C2-C6-Halogenalkenylsulfonyl, C3-C6-Alkinylthio, C3-C6-Alkinylsulfonyl, C3-C6-Ha-logenalkinylsulfonyl, C^Cg-Alkylamino, C2-C8-Dialkylamino, C3-C8-Dialkylaminocarbonyl, C3-C6-Trialkylsilyl, Thiazolyl, Phenyl, Pyrimidinyl oder Pyridyl ist, wobei das Thiazolyl, Phenyl, Pyridyl oder Pyrimidinyl gegebenenfalls mit 1-3 R20 substituiert sein kann; R31 unabhängig Halogen, Cyano, Nitro, C-j-Cg-Alkyl, C-pCg-Halogenalkyl, C-pCg-Hydroxyalkyl, C2-C6-Alkoxy-alkyl, C2-C6-Halogenalkoxyalkyl, C2-C6-Alkenyl, C2-C6-Halogenalkenyl, C3-C6-Alkinyl, C3-C6-Halogenalkinyl, Hydroxyl, C^Cg-Alkoxy, C^Cg-Halogenalkoxy, C2-C6-Alkenyloxy, C2-C6-Halogenalkenyloxy, C3-C6-Alkinyloxy, C3-C6-Halogenalkinyloxy, C^Cg-Alkylthio, C-pCg-Alkylsulfonyl, C^Cg-Halogenalkylsulfonyl, C2-C6-Alkenylthio, C2-Cg-Halogenalkenylthio, C2-C6-Halogenalkenylsulfonyl, C3-C6-Alkinylthio, C3-Cg-Alkinylsulfonyl, C3-C-6-Ha-logenalkinylsulfonyl, C1-C6-Alkylamino, C2-C8-Dialkylamino, C3-C8-Dialkylaminocarbonyl oder C3-C6-Trialkyl-silyl ist; R32 unabhängig: C^Cg-Alkyl, C^Cg-Halogenalkyl, C.|-Cg-Hydroxyalkyl, C2-C6-Alkoxyalkyl, C2-C6-Halogenalkoxyalkyl, C2-C6-Alkenyl, C2-C6-Halogenalkenyl, C3-C6-Alkinyl, C3-C6-Halogenalkinyl, Hydroxyl, C^Cg-Alkoxy, C^Cg-Halogenalkoxy, C2-C6-Alkenyloxy, C2-C6-Halogenalkenyloxy, C3-C6-Alkinyloxy, C3-C6-Halogenal-kinyloxy, C-j-Cg-Alkylthio, C1-C6-Alkylsulfonyl, C^Cg-Halogenalkylsulfonyl, C2-C6-Alkenylthio, C2-C6-Ha-logenalkenylthio, C2-C6-Halogenalkenylsulfonyl, C3-C6-Alkinylthio, C3-Cg-Alkinylsulfonyl, C3-C6-Halo-genalkinylsulfonyl, C-pCg-Alkylamino, C2-C8-Dialkylamino, C3-C8-Dialkylaminocarbonyl, C3-C6-Trialkylsi-lyi;
Phenyl, wobei der Phenylring gegebenenfalls mit 1-3 R20 substituiert sein kann; oder ein 5- oder 6-gliedriger gesättigter oder ungesättigter Ring, welcher 1-3 Heteroatome enthält, wobei jeder
Ring gegebenenfalls mit 1-3 R11 substituiert sein kann, ist; R33 unabhängig: C-j-Cg-Aikyl, C-j-Cg-Halogenalkyl, gegebenenfalls mit 1-3 R20 substituiertes Phenyl oder Thienyl; oder ein 5- oder 6-gliedriger gesättigter oder ungesättigter Ring, welcher 1-3 Heteroatome enthält, wobei jeder Ring gegebenenfalls mit 1-3 R11 substituiert sein kann, ist; R34: C-pCg-Alkyl, C^Cg-Halogenalkyl, C2-C6-Alkoxyalkyl, C1-C6-Alkylamino; oder ein 5- oder 6-gliedriger gesättigter oder ungesättigter Ring, welcher 1-3 Heteroatome enthält, wobei jeder Ring gegebenenfalls mit 1-3 R11 substituiert sein kann, ist; R35; C^Cg-Alkyl, C2-C6-Alkylcarbonyl; oder ein 5- oder 6-gliedriger gesättigter oder ungesättigter Ring, welcher 1-3 Heteroatome enthält, wobei jeder Ring gegebenenfalls mit 1-3 R11 substituiert sein kann, ist; R36 H, Cyano, C1-C6-Alkyl, C1-C6-Alkoxy, Benzyl oder Phenyl ist, wobei jedes Benzyl oder Phenyl gegebenenfalls mit 1-3 R20 substituiert sein kann; alternativ können R32 und R36 zusammengenommen sein, um: einen 5- oder 6-gliedrigen gesättigten oder ungesättigten Ring, welcher 1-3 Heteroatome enthält, wobei jeder Ring gegebenenfalls mit 1-3 R11 substituiert sein kann, zu bilden; und R37 unabhängig: H, Halogen oder gegebenenfalls mit 1-5 R20 substituiertes Phenyl; C1-C6-Alkyl, C1-C6-Halogenalkyl, Hydroxyl, C^Cg-Alkoxy oderC1-C6-Halogenalkoxy; oder ein 5- oder 6-gliedriger gesättigter oder ungesättigter Ring, welcher 1-3 Heteroatome enthält, wobei jeder
Ring gegebenenfalls mit 1-3 R11 substituiert sein kann, ist; zum Schutz einer Pflanze gegen Befall mit einem Pilzpathogen.
Revendications
1. Composé de formule I dans laquelle
- R1 représente un groupe de formule -N(R3)R4, - et R2 représente un groupe de formule -OR21 ; étant entendu que - R3 représente un atome d’hydrogène ; - R4 représente un atome d’hydrogène ; - R8 représente indépendamment un groupe alkyle en C^Cg, halogéno-alkyle en C-pCg, amino, (alkyle en CrCg)-amino ou (dialkyle en C2-C6)-amino, un groupe phényle, en option porteur de 1 à 3 substituant(s) R30, ou un groupe cyclique à 5 ou 6 chaînons, saturé ou insaturé, comportant 1 à 3 hétéroatome(s), et en option porteur, dans chaque cas, de 1 à 3 substituant(s) R11 ; - R11 représente indépendamment un atome d’halogène ou un groupe alkyle en C.|-Cg, halogéno-alkyle en C^Cg, alcoxy en C^Cg, halogéno-alcoxy en C-pCg, alkyl-thio en C-pCg, halogéno-alkyl-thio en C^Cg, amino, alkyl-amino en C-j-Cg, dialkyl-amino en C2-C6, alcoxy-carbonyle en C2-C6 ou alkyl-carbonyle en C2-C6 ; - R20 représente indépendamment un atome d’halogène, un groupe cyano, nitro, amino, alcoxy-alcoxy en C.|-Cg, alkyle en C-pCg, halogéno-alkyle en C-pCg, hydroxy-alkyle en CrC6, alcoxy-alkyle en C2-C6, halogéno-alcoxy-alkyle en C2-C6, alcényle en C2-C6, halogéno-alcényle en C2-C6, alcynyle en C3-C6, halogéno-alcynyle en C3-C6, hydroxyle, alcoxy en CrC6, halogéno-alcoxy en CrC6, alcényl-oxy en C2-C6, halogéno-alcényl-oxy en C2-C6, alcynyl-oxy en C3-C6, halogéno-alcynyl-oxy en C3-C6, alkyl-thio en C^Cg, halogéno-alkyl-thio en C^Cg, alkyl-sulfonyle en 0Γ06, halogéno-alkyl-sulfonyle en CrC6, alcényl-thio en C2-C6, halogéno-alcényl-this en C2-C6, halogéno-alcényl-sulfonyle en C2-C6, alcynyl-thio en C3-C6, alcynyl-sulfonyle en C3-C6, halogéno-alcy-nyl-sulfonyle en C3-C6, alkyl-amino en C.|-C6, dialkyl-amino en C2-C8, dialkyl-amino-carbonyle en C3-C8, alcoxy-carbonyle en C2-C6, alkyl-carbonyle en C2-C6 ou trialkyl-silyle en C3-C6, le groupe 2-((E)-méthoxy-imino)-N-méthyl-acétamido, un groupe phényle, benzyle, benzyloxyou phénoxy, ou un groupe hétérocyclique aromatique à 5 ou 6 chaînons, étant entendu que chacun de ces groupes phényle, benzyle, benzyl-oxy, phénoxy ou hétérocyclique aromatique à 5 ou 6 chaînons peut, en option, porter 1 à 3 substituant(s) choisi(s) indépendamment parmi les substituants R31; - R21 représente - un groupe alkyle en C.|-C14, - un groupe halogéno-alkyle en C^Cg, - un groupe alcényle en C2-C4, - un groupe halogéno-alcényle en C2-C4, - un groupe alcynyle en C3-C4, - un groupe halogéno-alcynyle en C3-C4, - un groupe phényle, naphtyle ou tétrahydro-quinoléinyle, en option porteur, dans chaque cas, de 1 à 3 substituant(s) R20, - un groupe de formule -(CHR22)mR23, - un groupe de formule -(CHR24)mC(0)0R25, - un groupe de formule -(CHR24)mC(0)R26, - un groupe de formule -(CHR24)mC(0)N(R27)R28, - un groupe de formule -(CHR24)mOR19, - un groupe de formule -(CHR24)mSR29, - un groupe de formule -(CHR24)mN(R27)R28, - un groupe de formule -C(=0)R32, - un groupe de formule -N=C(R32)(R36), - un groupe de formule -N(R25)C(=0)0R25, - un groupe de formule -Si(R8)3, - un groupe de formule -S02R33, - un groupe alcoxy-carbonyle en C2-C6, - un groupe alkyl-amino-carbonyle en C2-C6, - un groupe alkyl-carbonyle en C2-C6, - le reste d’un sucre choisi dans l’ensemble formé par les β-D-glucose-tétra-acétate, rhamnose, fructose et pentoses, - ou un groupe hétérocyclique aromatique à 5 ou 6 chaînons, choisi dans l’ensemble constitué par les groupes furanyle, pyridinyle, N-oxydo-pyridinyle, pyrimidinyle, pyridazinyle, pyrazinyle, pyrazolyle, thiazo-lyle, triazinyle, thiadiazolyle, oxazolyle, triazolyle et isoxazolyle, étant entendu que chacun de ces groupes hétérocycliques aromatiques à 5 ou 6 chaînons peut, en option, porter 1 à 5 substituant(s) R20, étant entendu que l’indice m est un nombre entier valant de 1 à 3 ; - R22 représente indépendamment - un atome d’hydrogène, - un atome d’halogène, - un groupe cyano, - un groupe nitro, - un groupe alkyle en C-j-Cg, - un groupe halogéno-alkyle en C^Cg, - un groupe phényle ou benzyle, en option porteur de 1 à 3 substituant(s) R20, - un groupe hydroxy-alkyle en C-j-Cg, - un groupe alcoxy-alkyle en C2-C6, - un groupe halogéno-alcynyle en C3-C6, - un groupe alcényle en C2-C6, - un groupe halogéno-alcényle en C2-C6, - un groupe alcynyle en C3-C6, - un groupe alcoxy en C^Cg, - un groupe halogéno-alcoxy en C^Cg, - un groupe alkyl-thio en C^Cg, - un groupe alkyl-amino en C-j-Cg, - un groupe dialkyl-amino en C2-C8, - un groupe cycloalkyl-amino en C3-C6, - un groupe (alkyl)-cycloalkyl-amino en C4-C6, - un groupe alkyl-carbonyle en C2-C6, - un groupe alcoxy-carbonyle en C2-C6, - un groupe alkyl-amino-carbonyle en C2-C6, - un groupe dialkyl-amino-carbonyle en C3-C8, - un groupe trialkyl-silyle en C3-C6, - un groupe hétérocyclique aromatique à cycles condensés, choisi dans l’ensemble formé par les groupes benzothiényle, quinoléinyle, isoquinoléinyle, thiéno[2,3-b]pyridyle, 1-méthyl-1H-thiéno[2,3-c]-pyrazolyle, et benzoimidazolyle, étant entendu que chacun des cycles peut en outre porter 1 à 3 substituant(s) R20, - ou un groupe hétérocyclique aromatique à 5 ou 6 chaînons, choisi dans l’ensemble constitué par les groupesfuranyle, pyridinyle, N-oxydo-pyridinyle, pyrimidinyle, pyridazinyle, pyrazinyle, thiazolyle, triazinyle, thiadiazolyle, oxazolyle, isoxazolyle, triazolyle et thiényle ; - R23 représente - un atome d’hydrogène, - un atome d’halogène, - un groupe alkyle en C.|-Cg, - un groupe halogéno-alkyle en C^Cg, - un groupe dialkyl-amino en C2-C6, - un groupe phényle, en option porteur de 1 à 5 substituant(s) R20, - un groupe hétérocyclique aromatique à cycles condensés, choisi dans l’ensemble formé par les groupes benzothiényle, quinoléinyle, isoquinoléinyle, thiéno[2,3-b]pyridyle, 1-méthyl-1H-thiéno[2,3-c]-pyrazolyle, benzofuranyle, benzoimidazolyle, 2,3-dihydro-benzo-furan-2-yle, 4-méthyl-4H-thiéno[3,2-b]pyrrol-5-yle, 1-méthyl-1 H-indol-5-yle, imidazo[1,2-a]pyridin-2-yle, imidazo[2,1-b]thiazol-6-yle, benzothiazol-2-yle, ben-zo[b]thiophèn-7-yle, et 1-méthyl-1 H-indazol-3-yle, étant entendu que chacun des cycles peut en outre porter 1 à 3 substituant(s) R20, - un groupe naphtyle, - un groupe benzo-1,3-dioxolyle, - un groupe pyrrolidinonyle, - un groupe oxétanyle, - un groupe alkyl-thio en C-pCg, en option porteur de 1 à 5 substituant(s) R20, - un groupe cyclique à 5 ou 6 chaînons, saturé ou insaturé, comportant 1 à 3 hétéroatome(s), étant entendu que chacun de ces cycles peut, en option, porter 1 à 3 substituant(s) R11, - ou un groupe hétérocyclique aromatique à 5 ou 6 chaînons, choisi dans l’ensemble constitué par les groupes furanyle, pyridinyle, N-oxydo-pyridinyle, pyrimidinyle, pyridazinyle, pyrazinyle, pyrazolyle, thiazolyle, triazinyle, thiadiazolyle, oxazolyle, isoxazolyle, triazolyle, imidazolyle, thiophèn-2-yle etthiophèn-3-yle, étant entendu que chacun de ces groupes hétérocycliques aromatiques peut, en option, porter 1 à 3 substituantes) R20 ; - R24 représente un atome d’hydrogène, un groupe alkyle en CrC6 ou alcoxy en CrC6, ou un groupe phényle ou benzyle, étant entendu que chacun de ces groupes phényle et benzyle peut, en option, porter 1 à 3 substituantes) R20; - R25 représente un atome d’hydrogène ou un groupe alkyle en C^Cg, phényle ou benzyle, en option porteur de 1 à 3 substituant(s) R20 ; - R26 représente - un atome d’hydrogène, - un groupe alkyle en C^Cg, - un groupe alcoxy en C-|-C6, - un groupe phényle, en option porteur de 1 à 3 substituant(s) R20, - ou un groupe hétérocyclique aromatique à 5 ou 6 chaînons, choisi dans l’ensemble constitué par les groupesfuranyle, pyridinyle, N-oxydo-pyridinyle, pyrimidinyle, pyridazinyle, pyrazinyle, thiazolyle, triazinyle, thiadiazolyle, oxazolyle, triazolyle et isoxazolyle ; - R27 et R28 représentent chacun, indépendamment, - un atome d’hydrogène, - un groupe alkyle en C.|-Cg, - un groupe phényle ou benzyle, étant entendu que chacun de ces groupes phényle et benzyle peut, en option, porter 1 à 3 substituant(s) R20, - ou un groupe cyclique à 5 ou 6 chaînons, saturé ou insaturé, comportant 1 à 3 hétéroatome(s), étant entendu que chacun de ces cycles peut, en option, porter 1 à 3 substituant(s) R11 ; - R29 représente - un atome d’hydrogène, - un groupe alkyle en CrC6, - un groupe halogéno-alkyle en C^Cg, - un groupe alcoxy-alkyle en C1-C6, - un groupe alkyl-carbonyle en C2-C6, - un groupe phényle ou benzyle, étant entendu que chacun de ces groupes phényle et benzyle peut, en option, porter 1 à 3 substituant(s) R20, - ou un groupe cyclique à 5 ou 6 chaînons, saturé ou insaturé, comportant 1 à 3 hétéroatome(s), étant entendu que chacun de ces cycles peut, en option, porter 1 à 3 substituant(s) R11 ; - R30 représente indépendamment un atome d’halogène, un groupe cyano, nitro, alkyle en C^Cg, halogéno-alkyle en C^Cg, hydroxyalkyle en C.|-Cg, alcoxy-alkyle en C2-C6, halogéno-alcoxy-alkyle en C2-C6, alcényle en C2-C6, halogéno-alcényle en C2-C6, alcynyle en C3-C6, halogéno-alcynyle en C3-C6, hydroxyle, alcoxy en C.|-Cg, halogéno-alcoxy en C1-C6, alcényl-oxy en C2-C6, halogéno-alcényloxy en C2-C6, alcynyl-oxy en C3-C6, halogéno-alcynyl-oxy en C3-C6, alkyl-thio en C^Cg, alkyl-sulfonyle en C-pCg, halogéno-alkyl-sulfonyle en C-pCg, alcényl-thio en C2-C6, halogéno-alcényl-thio en C2-C6, halogéno-alcényl-sulfonyle en C2-C6, alcynyl-thio en C3-C6, alcynyl-sulfonyle en C3-C6, halogéno-alcynyl-sulfonyle en C3-C6, alkyl-amino en C-pCg, dialkyl-amino en C2-C8, dialkyl-amino-carbonyle en C3-C8 ou trialkyl-silyle en C3-C6, ou un groupe thiazolyle, phényle, pyrimidinyle ou pyridinyle, étant entendu que chacun de ces groupes thiazolyle, phényle, pyridinyle ou pyrimidinyle peut, en option, porter 1 à 3 substituant(s) R20 ; - R31 représente indépendamment un atome d’halogène, un groupe cyano, nitro, alkyle en C-j-Cg, halogéno-alkyle en C-j-Cg, hydroxyalkyle en C-j-Cg, alcoxy-alkyle en C2-C6, halogéno-alcoxy-alkyle en C2-C6, alcényle en C2-C6, halogéno-alcényle en C2-C6, alcynyle en C3-C6, halogéno-alcynyle en C3-C6, hydroxyle, alcoxy en C-pCg, halogéno-alcoxy en C.|-Cg, alcényl-oxy en C2-C6, halogéno-alcényl-oxy en C2-C6, alcynyl-oxy en C3-C6, halogéno-alcynyl-oxy en C3-C6, alkyl-thio en C^Cg, alkyl-sulfonyle en C1-C6, halogéno-alkyl-sulfonyle en C1-C6, alcényl-thio en C2-C6, halogéno-alcényl-thio en C2-C6, halogéno-alcényl-sulfonyle en C2-C6, alcynyl-thio en C3-C6, alcynyl-sulfonyle en C3-C6, halogéno-alcynyl-sulfonyle en C3-C6, alkyl-amino en C-j-Cg, dialkyl-amino en C2-C8, dialkyl-amino-carbonyle en C3-C8 ou trialkyl-silyle en C3-C6 ; - R32 représente indépendamment - un groupe alkyle en CrC6, halogéno-alkyle en CrC6, hydroxy-alkyle en C1-C6, alcoxy-alkyle en C2-C6, halogéno-alcoxy-alkyle en C2-C6, alcényle en C2-C6, halogéno-alcényle en C2-C6, alcynyle en C3-C6, halogéno-alcynyle en C3-C6, hydroxyle, alcoxy en CrCg, halogéno-alcoxy en C1-C6, alcényl-oxy en C2-C6, halogéno-alcényl-oxy en C2-C6, alcynyl-oxy en C3-C6, halogéno-alcynyl-oxy en C3-C6, alkyl-thio en CrC6, alkyl-sulfonyle en C-pCg, halogéno-alkyl-sulfonyle en C^Cg, alcényl-thio en C2-C6, halogéno-alcényl-thio en C2-C6, halogéno-alcényl-sulfonyle en C2-C6, alcynyl-thio en C3-C6, alcynyl-sulfonyle en C3-C6, halogéno-alcynyl-sulfonyle en C3-C6, alkyl-amino en C-pCg, dialkyl-amino en C2-C8, dialkyl-amino-carbonyle en C3-C8 ou trialkyl-silyle en C3-C6, - un groupe phényle, lequel groupe phényle peut, en option, porter 1 à 3 substituant(s) R20, - ou un groupe cyclique à 5 ou 6 chaînons, saturé ou insaturé, comportant 1 à 3 hétéroatome(s), étant entendu que chacun de ces cycles peut, en option, porter 1 à 3 substituant(s) R11; - R33 représente indépendamment - un groupe alkyle en C.|-Cg, halogéno-alkyle en C^Cg, phényle ou thiényle, en option porteur de 1 à 3 substituant(s) R20, - ou un groupe cyclique à 5 ou 6 chaînons, saturé ou insaturé, comportant 1 à 3 hétéroatome(s), étant entendu que chacun de ces cycles peut, en option, porter 1 à 3 substituant(s) R11 ; - R34 représente - un groupe alkyle en C.|-Cg, halogéno-alkyle en C-pCg, alcoxy-alkyle en C2-C6 ou alkyl-amino en C.|-Cg, - ou un groupe cyclique à 5 ou 6 chaînons, saturé ou insaturé, comportant 1 à 3 hétéroatome(s), étant entendu que chacun de ces cycles peut, en option, porter 1 à 3 substituant(s) R11 ; - R35 représente - un groupe alkyle en C.|-Cg ou alkyl-carbonyle en C2-C6, - ou un groupe cyclique à 5 ou 6 chaînons, saturé ou insaturé, comportant 1 à 3 hétéroatome(s), étant entendu que chacun de ces cycles peut, en option, porter 1 à 3 substituant(s) R11 ; - R36 représente un atome d’hydrogène, un groupe cyano, alkyle en C-j-Cg ou alcoxy en C-j-Cg, ou un groupe benzyle ou phényle, étant entendu que chacun de ces groupes benzyle ou phényle peut, en option, porter 1 à 3 substituant(s) R20 ; - ou autrement, R32 et R36 peuvent représenter des entités qui forment conjointement un groupe cyclique à 5 ou 6 chaînons, saturé ou insaturé, comportant 1 à 3 hétéroatome(s), étant entendu que chacun de ces cycles peut, en option, porter 1 à 3 substituant(s) R11 ; - et R37 représente indépendamment - un atome d’hydrogène ou d’halogène, ou un groupe phényle, en option porteur de 1 à 5 substituants) R20, - un groupe alkyle en C-pCg, halogéno-alkyle en C1-C6, hydroxyle, alcoxy en C-pCg ou halogéno-alcoxy en Ci-C6, - ou un groupe cyclique à 5 ou 6 chaînons, saturé ou insaturé, comportant 1 à 3 hétéroatome(s), étant entendu que chacun de ces cycles peut, en option, porter 1 à 3 substituant(s) R11 ; sous réserve que le composé ne soit pas une 4-amino-5-fluoro-2-[tris-(alkyl en C-pCjj-silyl-oxyj-pyrimidine, la 2-éthoxy-4-amino-5-fluoro-pyrimidine ou la 2-méthoxy-4-amino-5-fluoro-pyrimidine. 2. Composé de formule I, conforme à la revendication 1, dans lequel - R3 représente un atome d’hydrogène ; - R4 représente un atome d’hydrogène ; - R21 représente un groupe de formule -C(=0)R32, -N=C(R32)(R36), -S02R33 ou -N(R25)C(=0)0R25, ou un groupe alkyle en CrCg ou alcoxy en CrC6 ; - R25 représente un atome d’hydrogène ou un groupe alkyle en C-j-Cg ; - R32 représente un groupe alkyle en C1-C6, ou un groupe phényle qui peut, en option, porter 1 à 3 substituant(s) R20 ; - R33 représente un groupe alkyle en C.|-Cg, phényle ou thiényle, en option porteur de 1 à 3 substituant(s) R20 ; - R36 représente un groupe cyano ou alkyle en C1-C6 ou un groupe phényle qui peut, en option, porter 1 à 3 substituant(s) R20 ; - et R20 représente un atome d’halogène ou un groupe alkyle en C-j-Cg ou alcoxy en C-pCg. 3. Composé de formule I, conforme à la revendication 1, dans lequel - R3 représente un atome d’hydrogène ; - R4 représente un atome d’hydrogène ; - R21 représente un groupe de formule -(CHR22)mR23 où l’indice m vaut 1 ; - R22 représente un atome d’hydrogène ou un groupe alkyle en C.1-C4 ou phényle ; - R23 représente un groupe hétérocyclique aromatique à cycles condensés, choisi dans l’ensemble formé par les groupes benzothiényle, quinoléinyle, isoquinoléinyle, thiéno[2,3-b]pyridyle, 1-méthyl-1 H-thiéno[2,3-c]-pyra-zolyle, benzofuranyle, benzoimidazolyle, 2,3-dihydro-benzo-furan-2-yle, 4-méthyl-4H-thiéno[3,2-b]pyrrol-5-yle, 1 -méthyl-1 H-indol-5-yle, imidazo[1,2-a]pyridin-2-yle, imidazo-[2,1-b]thiazol-6-yle, benzothiazol-2-yle, ben-zo[b]thiophèn-7-yle et 1-méthyl-1 H-indazol-3-yle, étant entendu que chacun des cycles peut en outre porter 1 à 3 substituant(s) R20 ; - et R20 représente un atome d’halogène ou un groupe alkyle en C.|-Cg ou alcoxy en C-pCg. 4. Composé de formule I, conforme à la revendication 1, dans lequel - R3 représente un atome d’hydrogène ; - R4 représente un atome d’hydrogène ; - R21 représente un groupe de formule -(CHR22)mR23 où l’indice m vaut 1 ; - R22 représente un atome d’hydrogène ; - et R23 représente un groupe cyclique à 5 ou 6 chaînons, saturé ou insaturé, comportant 1 à 3 hétéroatome(s), étant entendu que chacun de ces cycles peut, en option, porter 1 à 3 substituant(s) R11. 5. Composé de formule I, conforme à la revendication 1, dans lequel - R3 représente un atome d’hydrogène ; - R4 représente un atome d’hydrogène ; - R21 représente un groupe de formule -(CHR22)mR23 où l’indice m vaut 1 ; - R22 représente un atome d’hydrogène ; - R23 représente un groupe hétérocyclique aromatique à 5 ou 6 chaînons, choisi dans l’ensemble constitué par lesgroupesfuranyle, pyridinyle, N-oxydo-pyridinyle, pyrimidinyle, pyridazinyle, pyrazinyle, pyrazolyle.thiazolyle, triazinyle, thiadiazolyle, oxazolyle, isoxazolyle, triazolyle, imidazolyle, thiophèn-2-yle, thiophèn-3-yle et 1-mé-thyl-1 H-pyrazol-3-yle, étant entendu que chacun de ces groupes hétérocycliques aromatiques peut, en option, porter 1 à 3 substituant(s) R20 ; - et R20 représente un atome d’halogène ou un groupe nitro, alkyle en C-pCg ou alcoxy en C-j-Cg. 6. Composé de formule I, conforme à la revendication 1, dans lequel - R3 représente un atome d’hydrogène ; - R4 représente un atome d’hydrogène ; - R21 représente un groupe de formule -(CHR22)mR23 où l’indice m vaut 1 ; - R22 représente un groupe alkyle en C-pCg ou phényle, en option porteur de 1 à substituant(s) R20 ; - R23 représente un groupe naphtyle ou phényle, en option porteur de 1 à 5 substituant(s) R20 ; - R20 représente un atome d’halogène ou un groupe nitro, alkyle en C-pCg, alcoxy en C-pCg, phénoxy ou phényle, étant entendu que chacun de ces groupes phényle ou phénoxy peut, en option, porter 1 à 3 substituant(s) indépendamment choisi(s) parmi les substituants R31 ; - et R31 représente un atome d’halogène ou un groupe alkyle en C-pCg, halogéno-alkyle en C-pCg, benzyle ou pyridinyle. 7. Composé de formule I, conforme à la revendication 1, dans lequel - R3 représente un atome d’hydrogène ; - R4 représente un atome d’hydrogène ; - R21 représente un groupe de formule -(CHR22)mR23 où l’indice m vaut 1 ; - R22 représente un atome d’hydrogène ; - R23 représente un groupe naphtyle, benzo-1,3-dioxolyle ou phényle, en option porteur de 1 à 5 substituant(s) R20; - R20 représente un atome d’halogène ou un groupe cyano, nitro, amino, alcoxy-alcoxy en C-j-Cg, alkyle en C.|-Cg, halogéno-alkyle en C.|-Cg, hydroxy-alkyle en C^Cg, alcoxy-alkyle en C2-C6, halogéno-alcoxy-alkyle en C2-C6, alcényle en C2-C6, hydroxyle, alcoxy en C^Cg, halogéno-alcoxy en C.|-Cg, alkyl-thio en C^Cg, halogéno-alkyl-thio en C1-C6, alkyl-sulfonyle en CrC6, alkyl-amino en CrC6, benzyl-oxy ou phénoxy, étant entendu que chacun de ces groupes benzyl-oxy ou phénoxy peut, en option, porter 1 à 3 substituant(s) indépendamment choisi(s) parmi les substituants R31 ; - et R31 représente un atome d’halogène ou un groupe alkyle en C-j-Cg ou alcoxy en C-pCg. 8. Composé de formule I, conforme à la revendication 1, dans lequel - R3 représente un atome d’hydrogène ; - R4 représente un atome d’hydrogène ; - R21 représente un groupe de formule -(CHR22)mR23 où l’indice m vaut 1 ; - R22 représente un groupe de formule -CH3, -CH2CH3 ou -CH2CH2-CH3, ou un groupe benzyle ou 4-fluoro-phényle; - et R23 représente un groupe phényle, 4-fluoro-phényle ou para-tolyle. 9. Composé de formule I, conforme à la revendication 1, dans lequel - R3 représente un atome d’hydrogène ; - R4 représente un atome d’hydrogène ; - R21 représente un groupe de formule -(CHR22)mR23 où l’indice m vaut 1 ; - R22 représente un atome d’hydrogène ; - et R23 représente un groupe phényle, para-tolyle, 4-fluoro-phényle, 4-méthoxy-phényle, 3-méthoxy-phényle, thiophèn-2-yle, thiophèn-3-yle, 3-fluoro-phényle, 3-bromo-phényle, benzo-thiophèn-2-yle, 2,4,6-triméthyl-phé-nyle, 1-éthyl-2-méthoxy-phényle, 3-cyano-phényle ou 3-fluoro-4-méthoxy-phényle. 10. Composé de formule I, conforme à la revendication 1, choisi parmi les suivants :
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11. Composition destinée à la lutte contre un pathogène fongique, comprenant un composé conforme à l’une des revendications 1 à 10, et un matériau support phytologiquement admissible. 12. Composition conforme à la revendication 11, pour laquelle le pathogène fongique est l’un des suivants : tavelure du pommier (Venturis inaequalis), nuile des céréales (Septoria tritici), cercosporiose de la betterave (Cercospora beticola), cercosporiose de l’arachide (Cercospora arachidicola), et cercosporiose noire (Mycosphaerella fijiensis). 13. Procédé de lutte et de prévention contre une attaque fongique sur un végétal, lequel procédé comporte une étape consistant à appliquer, en une quantité à effet fongicide, au moins l’un des composés conformes à l’une des revendications 1 à 10 sur au moins l’un des objectifs suivants : le végétal lui-même, une zone adjacente au végétal, un sol adapté pour soutenir la pousse du végétal, une racine du végétal, le feuillage du végétal, et de la semence adaptée pour la production d’au moins l’un du végétal lui-même et d’un autre végétal. 14. Utilisation d’un composé de formule I : dans laquelle
- R1 représente un groupe de formule -N(R3)R4, - et R2 représente un groupe de formule -OR21 ; étant entendu que - R3 représente un atome d’hydrogène ; - R4 représente un atome d’hydrogène ; - R8 représente indépendamment un groupe alkyle en C-j-Cg, halogéno-alkyle en C-j-Cg, amino, (alkyle en C^Cgj-amino ou (dialkyle en C2-C6)-amino, un groupe phényle, en option porteur de 1 à 3 substituant(s) R30, ou un groupe cyclique à 5 ou 6 chaînons, saturé ou insaturé, comportant 1 à 3 hétéroatome(s), et en option porteur, dans chaque cas, de 1 à 3 substituant(s) R11 ; - R11 représente indépendamment un atome d’halogène ou un groupe alkyle en C-j-Cg, halogéno-alkyle en CrC6, alcoxy en CrC6, halogéno-alcoxy en CrC6, alkyl-thio en CrC6, halogéno-alkyl-thio en C-pCg, amino, alkyl-amino en C-j-Cg, dialkyl-amino en C2-C6, alcoxy-carbonyle en C2-C6 ou alkyl-carbonyle en C2-C6 ; - R20 représente indépendamment un atome d’halogène, un groupe cyano, nitro, amino, alcoxy-alcoxy en C-pCg, alkyle en C-pCg, halogéno-alkyle en C-pCg, hydroxy-alkyle en C-pCg, alcoxy-alkyle en C2-C6, halogéno-alcoxy-alkyle en C2-C6, alcényle en C2-C6, halogéno-alcényle en C2-C6, alcynyle en C3-C6, halogéno-alcynyle en C3-C6, hydroxyle, alcoxy en C-j-Cg, halogéno-alcoxy en C-j-Cg, alcényl-oxy en C2-C6, halogéno-alcényl-oxy en C2-C6, alcynyl-oxy en C3-C6, halogéno-alcynyl-oxy en C3-C6, alkyl-thio en C1-C6, halogéno-alkyl-thio en C1-C6, alkyl-sulfonyle en CrC6, halogéno-alkyl-sulfonyle en C1-C6, alcényl-thio en C2-C6, halogéno-alcényl-thio en C2-C6, halogéno-alcényl-sulfonyle en C2-C6, alcynyl-thio en C3-C6, alcynyl-sulfonyle en C3-C6, halogéno-alcy-nyl-sulfonyle en C3-C6, alkyl-amino en C-pCg, dialkyl-amino en C2-C8, dialkyl-amino-carbo-nyle en C3-C8, alcoxy-carbonyle en C2-C6, alkyl-carbonyle sen C2-C6ou trialkyl-silyle en C3-C6, le groupe 2-((E)-méthoxy-imino)-N-méthyl-acétamido, un groupe phényle, benzyle, benzyloxy ou phénoxy, ou un groupe hétérocyclique aromatique à 5 ou 6 chaînons, étant entendu que chacun de ces groupes phényle, benzyle, benzyl-oxy, phénoxy ou hétérocyclique aromatique à 5 ou 6 chaînons peut, en option, porter 1 à 3 substituant(s) choisi(s) indépendamment parmi les substituants R31 ; - R21 représente - un groupe alkyle en CyCu, - un groupe halogéno-alkyle en Ci-C6, - un groupe alcényle en C2-C4, - un groupe halogéno-alcényle en C2-C4, - un groupe alcynyle en C3-C4, - un groupe halogéno-alcynyle en C3-C4, - un groupe phényle, naphtyle ou tétrahydro-quinoléinyle, en option porteur, dans chaque cas, de 1 à 3 substituant(s) R20, - un groupe de formule -(CHR22)mR23, - un groupe de formule -(CHR24)mC(0)0R25, - un groupe de formule -(CHR24)mC(0)R26, - un groupe de formule -(CHR24)mC(0)N(R27)R28, - un groupe de formule -(CHR24)mOR29, - un groupe de formule -(CHR24)mSR29, - un groupe de formule -(CHR24)mN(R27)R28, - un groupe de formule -C(=0)R32, - un groupe de formule -N=C(R32)(R36), - un groupe de formule -N(R25)C(=0)0R25, - un groupe de formule -Si(R8)3, - un groupe de formule -S02R33, - un groupe alcoxy-carbonyle en C2-C6, - un groupe alkyl-amino-carbonyle en C2-C6, - un groupe alkyl-carbonyle en C2-C6, - le reste d’un sucre choisi dans l’ensemble formé par les β-D-glucose-tétra-acétate, rhamnose, fructose et pentoses, - ou un groupe hétérocyclique aromatique à 5 ou 6 chaînons, choisi dans l’ensemble constitué par les groupes furanyle, pyridinyle, N-oxydo-pyridinyle, pyrimidinyle, pyridazinyle, pyrazinyle, pyrazolyle, thiazo-lyle, triazinyle, thiadiazolyle, oxazolyle, triazolyle et isoxazolyle, étant entendu que chacun de ces groupes hétérocy-cliques aromatiques à 5 ou 6 chaînons peut, en option, porter 1 à 5 substituant(s) R20 ; - R22 représente indépendamment - un atome d’hydrogène, - un atome d’halogène, - un groupe cyano, - un groupe nitro, - un groupe alkyle en C-pCg, - un groupe halogéno-alkyle en C-pCg, - un groupe phényle ou benzyle, en option porteur de 1 à 3 substituants) R20, - un groupe hydroxy-alkyle en C-pCg, - un groupe alcoxy-alkyle en C2-C6, - un groupe halogéno-alcynyle en C3-C6, - un groupe alcényle en C2-C6, - un groupe halogéno-alcényle en C2-C6, - un groupe alcynyle en C3-C6, - un groupe alcoxy en C-pCg, - un groupe halogéno-alcoxy en C.|-Cg, - un groupe alkyl-thio en C.|-Cg, - un groupe alkyl-amino en C^Cg, - un groupe dialkyl-amino en C2-C8, - un groupe cycloalkyl-amino en C3-C6, - un groupe (alkyl)-cycloalkyl-amino en C4-C6, - un groupe alkyl-carbonyle en C2-C6, - un groupe alcoxy-carbonyle en C2-C6, - un groupe alkyl-amino-carbonyle en C2-C6, - un groupe dialkyl-amino-carbonyle en C3-C8, - un groupe trialkyl-silyle en C3-C6, - un groupe hétérocyclique aromatique à cycles condensés, choisi dans l’ensemble formé par les groupes benzothiényle, quinoléinyle, isoquinoléinyle, thiéno[2,3-b]pyridyle, 1-méthyl-1 H-thiéno[2,3-c]-pyrazolyle, et benzoimidazolyle, étant entendu que chacun des cycles peut en outre porter 1 à 3 substituant(s) R20, - ou un groupe hétérocyclique aromatique à 5 ou 6 chaînons, choisi dans l’ensemble constitué par les groupesfuranyle, pyridinyle, N-oxydo-pyridinyle, pyrimidinyle, pyridazinyle, pyrazinyle, thiazolyle, triazinyle, thiadiazolyle, oxazolyle, isoxazolyle, triazolyle et thiényle ; - R23 représente - un atome d’hydrogène, - un atome d’halogène, - un groupe alkyle en 0Γ06, - un groupe halogéno-alkyle en C^Cg, - un groupe dialkyl-amino en C2-C6, - un groupe phényle, en option porteur de 1 à 5 substituant(s) R20, - un groupe hétérocyclique aromatique à cycles condensés, choisi dans l’ensemble formé par les groupes benzothiényle, quinoléinyle, isoquinoléinyle, thiéno[2,3-b]pyridyle, 1-méthyl-1 H-thiéno[2,3-c]-pyrazolyle, benzofuranyle, benzoimidazolyle, 2,3-dihydro-benzo-furan-2-yle, 4-méthyl-4H-thiéno[3,2-b]pyrrol-5-yle, 1-méthyl-1H-indol-5-yle, imidazo[1,2-a]pyridin-2-yle, imidazo[2,1-b]thiazol-6-yle, benzothiazol-2-yle, ben-zo[b]thiophèn-7-yle, et 1-méthyl-1 H-indazol-3-yle, étant entendu que chacun des cycles peut en outre porter 1 à 3 substituant(s) Rzo, - un groupe naphtyle, - un groupe benzo-1,3-dioxolyle, - un groupe pyrrolidinonyle, - un groupe oxétanyle, - un groupe alkyl-thio en CrC6, en option porteur de 1 à 5 substituant(s) R20, - un groupe cyclique à 5 ou 6 chaînons, saturé ou insaturé, comportant 1 à 3 hétéroatome(s), étant entendu que chacun de ces cycles peut, en option, porter 1 à 3 substituant(s) R11, - ou un groupe hétérocyclique aromatique à 5 ou 6 chaînons, choisi dans l’ensemble constitué par les groupes furanyle, pyridinyle, N-oxydo-pyridinyle, pyrimidinyle, pyridazinyle, pyrazinyle, pyrazolyle, thiazolyle, triazinyle, thiadiazolyle, oxazolyle, isoxazolyle, triazolyle, imidazolyle, thiophèn-2-yle etthiophèn-3-yle, étant entendu que chacun de ces groupes hétérocycliques aromatiques peut, en option, porter 1 à 3 substituants) R20 ; - R24 représente une atome d’hydrogène, un groupe alkyle en C-j-Cg ou alcoxy en C1-C6, ou un groupe phényle ou benzyle, étant entendu que chacun de ces groupes phényle et benzyle peut, en option, porter 1 à 3 substituants) R20 ; - R25 représente un atome d’hydrogène ou un groupe alkyle en C-j-Cg, phényle ou benzyle, en option porteur de 1 à 3 substituant(s) R20 ; - R26 représente - un atome d’hydrogène, - un groupe alkyle en C-j-Cg, - un groupe alcoxy en C-pCg, - un groupe phényle, en option porteur de 1 à 3 substituant(s) R20, - ou un groupe hétérocyclique aromatique à 5 ou 6 chaînons, choisi dans l’ensemble constitué par les groupes furanyle, pyridinyle, N-oxydo-pyridinyle, pyrimidinyle, pyridazinyle, pyrazinyle, thiazolyle, triazinyle, thiadiazolyle, oxazolyle, triazolyle et isoxazolyle ; - R27 et R28 représentent chacun, indépendamment, - un atome d’hydrogène, - un groupe alkyle en C^Cg, - un groupe phényle ou benzyle, étant entendu que chacun de ces groupes phényle et benzyle peut, en option, porter 1 à 3 substituant(s) R20, - ou un groupe cyclique à 5 ou 6 chaînons, saturé ou insaturé, comportant 1 à 3 hétéroatome(s), étant entendu que chacun de ces cycles peut, en option, porter 1 à 3 substituant(s) R11 ; - R29 représente - un atome d’hydrogène, - un groupe alkyle en Ci-C6, - un groupe halogéno-alkyle en C^Cg, - un groupe alcoxy-alkyle en C^Cg, - un groupe alkyl-carbonyle en C2-C6, - un groupe phényle ou benzyle, étant entendu que chacun de ces groupes phényle et benzyle peut, en option, porter 1 à 3 substituant(s) R20, - ou un groupe cyclique à 5 ou 6 chaînons, saturé ou insaturé, comportant 1 à 3 hétéroatome(s), étant entendu que chacun de ces cycles peut, en option, porter 1 à 3 substituant(s) R11 ; - R30 représente indépendamment un atome d’halogène, un groupe cyano, nitro, alkyle en C^Cg, halogéno-alkyle en C^Cg, hydroxy-alkyle en C^Cg, alcoxy-alkyle en C2-C6, halogéno-alcoxy-alkyle en C2-C6, alcényle en C2-C6, halogéno-alcényle en C2-C6, alcynyle en C3-C6, halogéno-alcynyle en C3-C6, hydroxyle, alcoxy en C-|-Cg, halogéno-alcoxy en C-pCg, alcényl-oxy en C2-C6, halogéno-alcényl-oxy en C2-C6, alcynyl-oxy en C3-C6, halogéno-alcynyl-oxy en C3-C6, alkyl-thio en C-j-Cg, alkyl-sulfonyle en C-j-Cg, halogéno-alkyl-sulfonyle en C1-C6, alcényl-thio en C2-C6, halogéno-alcényl-thio en C2-C6, halogéno-alcényl-sulfonyle en C2-C6, alcynyl-thio en C3-C6, alcynyl-sulfonyle en C3-C6, halogéno-alcynyl-sulfonyle en C3-C6, alkyl-amino en C-pCg, dialkyl-amino en C2-C8, dialkyl-amino-carbonyle en C3-C8 ou trialkyl-silyle en C3-C6, ou un groupe thiazolyle, phényle, pyri-midinyle ou pyridinyle, étant entendu que chacun de ces groupes thiazolyle, phényle, pyridinyle ou pyrimidinyle peut, en option, porter 1 à 3 substituant(s) R20 ; - R31 représente indépendamment un atome d’halogène, un groupe cyano, nitro, alkyle en C^Cg, halogéno-alkyle en C^Cg, hydroxy-alkyle en C-j-Cg, alcoxy-alkyle en C2-C6, halogéno-alcoxy-alkyle en C2-C6, alcényle en C2-C6, halogéno-alcényle en C2-C6, alcynyle en C3-C6, halogéno-alcynyle en C3-C6, hydroxyle, alcoxy en CrC6, halogéno-alcoxy en C^-Cg, alcényl-oxy en C2-C6, halogéno-alcényl-oxy en C2-C6, alcynyl-oxy en C3-C6, halogén.o-alcynyl-oxy en C3-C6, alkyl-thio en CrC6, alkyl-sulfonyle en C-pCg, halogéno-alkyl-sulfonyle en C1-C6, alcényl-thio en C2-C6, halogéno-alcényl-thio en C2-C6, halogéno-alcényl-sulfonyle en C2-C6, alcynyl-thio en C3-C6, alcynyl-sulfonyle en C3-C6, halogéno-alcynyl-sulfonyle en C3-C6, alkyl-amino en C-|-C6, dialkyl-amino en C2-C8, dialkyl-amino-carbonyle en C3-C8 ou trialkyl-silyle en C3-C6 ; - R32 représente indépendamment - un groupe alkyle en C^Cg, halogéno-alkyle en 0Γ06, hydroxy-alkyle en C^Cg, alcoxy-alkyle en C2-C6, halogéno-alcoxy-alkyle en C2-C6, alcényle en C2-C6, halogéno-alcényle en C2-C6, alcynyle en C3-C6, halogéno-alcynyle en C3-C6, hydroxyle, alcoxy en CrC6, halogéno-alcoxy en C^Cg, alcényl-oxy en C2-C6, halogéno-alcényl-oxy en C2-C6, alcynyl-oxy en C3-C6, halogéno-alcynyl-oxy en C3-C6, alkyl-thio en CrC6, alkyl-sulfonyle en C^Cg, halogéno-alkyl-sulfonyle en C^Cg, alcényl-thio en C2-C6, halogéno-alcényl-thio en C2-C6, halogéno-alcényl-sulfonyle en C2-C6, alcynyl-thio en C3-C6, alcynyl-sulfonyle en C3-C6, halogéno-alcynyl-sulfonyle en C3-C6, alkyl-amino en CrC6, dialkyl-amino en C2-C8, dialkyl-amino-carbonyle en C3-C8 ou trialkyl-silyle en C3-C6, - un groupe phényle, lequel groupe phényle peut, en option, porter 1 à 3 substituant(s) R20, - ou un groupe cyclique à 5 ou 6 chaînons, saturé ou insaturé, comportant 1 à 3 hétéroatome(s), étant entendu que chacun de ces cycles peut, en option, porter 1 à 3 substituant(s) R11 ; - R33 représente indépendamment - un groupe alkyle en C^Cg, halogéno-alkyle en CrC6, phényle ou thiényle, en option porteur de 1 à 3 substituant(s) R20, - ou un groupe cyclique à 5 ou 6 chaînons, saturé ou insaturé, comportant 1 à 3 hétéroatome(s), étant entendu que chacun de ces cycles peut, en option, porter 1 à 3 substituant(s) R11 ; - R34 représente - un groupe alkyle en CrCg, halogéno-alkyle en CrC6, alcoxy-alkyle en C2-C6 ou alkyl-amino en C^Cg, - ou un groupe cyclique à 5 ou 6 chaînons, saturé ou insaturé, comportant 1 à 3 hétéroatome(s), étant entendu que chacun de ces cycles peut, en option, porter 1 à 3 substituant(s) R11 ; - R35 représente - un groupe alkyle en CrC6 ou alkyl-carbonyle en C2-C6, - ou un groupe cyclique à 5 ou 6 chaînons, saturé ou insaturé, comportant 1 à 3 hétéroatome(s), étant entendu que chacun de ces cycles peut, en option, porter 1 à 3 substituant(s) R11 ; - R36 représente un atome d’hydrogène, un groupe cyano, alkyle en C^Cg ou alcoxy en C-pCg, ou un groupe benzyle ou phényle, étant entendu que chacun de ces groupes benzyle ou phényle peut, en option, porter 1 à 3 substituant(s) R20 ; - ou autrement, R32 et R36 peuvent représenter des entités qui forment conjointement un groupe cyclique à 5 ou 6 chaînons, saturé ou insaturé, comportant 1 à 3 hétéroatome(s), étant entendu que chacun de ces cycles peut, en option, porter 1 à 3 substituant(s) R11 ; - et R37 représente indépendamment - un atome d’hydrogène ou d’halogène, ou un groupe phényle, en option porteur de 1 à 5 substituants) R20, - un groupe alkyle en C^Cg, halogéno-alkyle en C^Cg, hydroxyle, alcoxy en C^Cg ou halogéno-alcoxy en Ci-C6, - ou un groupe cyclique à 5 ou 6 chaînons, saturé ou insaturé, comportant 1 à 3 hétéroatome(s), étant entendu que chacun de ces cycles peut, en option, porter 1 à 3 substituant(s) R11 ; pour protéger un végétal contre une attaque d’un pathogène fongique.

Claims (7)

S2AEAÖMM IGÉNYPONTOK .1,:0} képlet« vegyük«S2AEAÖMM YOUR POINTS .1,: 0} Take It « ahol R! jelentése -N(R')R4; R? jelentése <β?; R? jelentése H; R~ jelentése H; Rs jelentése egymástól függetlenül CrG. akii, C.4'&amp; haloalkil amiao, C-C* alkíiammo, CVG diaiküamma lesül, amely adott esetben sktíkseutaáií vagy 5- vagy 6- tagú telisen vagy telítetlen gyűrű, amely I-3 hetesoatomot tartalmas, ahol valamennyi gyűrő adott esetben szufesxütuáit 1-3 Rí! srtOsxtkieessei; I5:i jéteése e#máetól;fílgptisídii: Imlogén,: €rCs alkli, baloalkll, COOs «}koxt,:Cs-€s bsloGGxl, Ci-Cÿ alkütte, O;.¾ Mealklbk, snütsó, GiRlgalkllamme, ülalkiasíjino, CrOs alkoxlkarbonik vagy CgCk aMkaiéóntl; Rí!) jétaése egymástól Ilggetlenil bálegén, elásk, ainy annno, ÜrG afkokalkmi, C>€« aikif, CeG bálnáid!, COQ kdtóxiáMi, Q.-C^ alkonialldt, GjRds/baloalkoxkffel, CrC* alkenib C^Gy Isloalkeall €>·€<, álkínií G-G báfoakinii hidrexib €rG, A<«á, CrOOkloalkop, 1¾^¾ slkeniloxi Cv-€* baloalkemloxi,: :ÓrC*a!kinnok, G3:Rly ·0Α alk|$% 0.Ä !mioüMMo,: OjdŰ^á&amp;átoMbötksOt-Cé ímloalkisgulloni, CrC* albetültky Cj-Cs Mealketúko,: CrÓ| WoaíkemlsxOíbníi C^Gs alkiníítlo,: CrG-v GiiráÉgüilosst!, CÄ ba!oa!klmfe2tűlóiiÍ,: G t-Gg alkűaskno, €rCS; slialkiknáno, C ^-Gs dlsMlapmokarbonsi, €rQ, níkoxiknkmii, €.;··€> aikiikarbonil, C trialkdsxiisl, i-líEy isetoxIűssíísojd^-sBeölmeetasnMil, fenil, benOI, benxked, fenoxi, vagy 5- vagy 6- tagú heteroaromas gyűrű, akti valansensyí lead, benzil, besspioxi, fenoxi. vagy 5- vagy 6 - nsgíTtóenstroistáé gyűrű adott esetben sxnbMÜniÜ 1 -3 xtmbsxiksnesseL smefy egy-mástél fegstlsnül lO fâ&amp;t tnegválasaktp 10! jelentése: CrGss aikd. €<-€* bálna tksl; CrG4 alkenü; CrCi haloalkenü; ti äs s ^ rstteuv «T p * ?«$ «t&amp;a síi CrCs alkioil; CrC4 haloalkioik f«sdl, ru5ltü, vagy tetrahsdrokinolinu, vdarnenny- adott esetben szubsauívált i-3 R* ^ubs^íúiamssel, -(CHro*Rs; -íCHRm):^(0)ORsí «(CHRî4>.ù^Û>R2% iCHR-4}:::C(0}N(R27}R^; •(CHRî4):::ORj<î; (CHR:î4}iy$iÎS (CHR24):;^#7)^ •C(»0}Rî;!; -«p5í)ít^ -NR?X'b<bOR;'-: •Si(R\; -SOjRr>; C2-C(: alRoaikaohottb; Gî-Cÿ: alRiïttmooRsrhool!:; €rC<; ákilkarboMl;: évkor, amely bsía-ö-glaMis4eiíaaeeíáR Inïktàx, ës f emë® ©sp|)ort|#3Ôi xaggválasziöM;; vagy 5~ vagy $- :gyM, amely íkraol, prlbmi, p!íaÍMRbl-í>xM, gkkxbdxml, pxidasíxbl, |#miÄ fÉæ&amp;e&amp;i, xíaaoll,; Mpskil, tmdmaolik oppdÉ, xdagottl vagy Ipxaæegi. csoporf áMI xmígvá^· lakott, almi valaxvexixxyl I- vagy '6- tagú beimssp^íSs. 0%&amp; adott RS R® ^bsaitaaBgsel; áká m értéke í -3 egesa Mám; W jekMésaiegygíásXél f%göí!exáik H; balogé«.;: eiaxm; ráíró; CVC* alkil: Cí“€a Míoaikil; fesd: vagy bemdl, mxxely adott:vseitex saabkaid«ált 1-3 ll^sxebsiditttmssá:; €:-€,> bidroxialk-l; CrCö alkoxílalkil; CrQ, haloalkiad; C;rCí, alkexdi; C;r-C* Ixateaikepxi;; \ í ··(.·,<. UÍívfe': !< C-rC's aîkcxi. C;-€ft haloaikoxi; C;”C.<. aikiltk*; CrQ aikUainiao; CyCh diaîki lasmoo; OC. olkkalkikrmrso; C ,-Cs i.aíi^ sc'k;'tólk'l‘i"í::no; Cr('fc alkiSkarbomi; Cj-Cft askoxikarbotnÈ; Cri'* aUcilamisokarbosùl; C.rCs dialksiamsaokarboail; CrCétsâaiëkKlIil' koadteœilt itomaîmnâs gyűrű, mxà? kinoand, jiæbklboli ti«®o£23*Mp^*l< * ' 3Tæd!*l:E4leso|23'C|aira^!0!; es Isesizôimifeôii ca&amp;pordâbô] Äl^Äe-toyi.győri îwalfe khs$ X-% axuk&amp;kltaebssel;; vagy 5- vagy 6- tagú heteroarcmás gyüm a»sdÿ plÂi» pMiSäÄali JtlfaÉl, plraziaih uaæoUl trkxinii, badiaxoll* 1*8, ix&amp;yaaxÄ tánaobl és tímü osösortjábél megválása wb; R^jdeniéss: H; i-alogéa; CrQalkü; Ct-C, haioalkii; CrQ, dkűkaarohio; térni aînsîliy adod nseíhm s^ibsstimák 1-5 R"'* srabsæituei&amp;sei b«öx)&amp;fssl: és bgkaoissída^lik ;23^fcà%^»ba»fesaa-2--il« d-œotl- 4iRíteop:Jd>Jpírmb5-I, beb«ikaoR2'llybebzo{l?|iól«0'ídi és l-mei^iM-mbaaol^-ji ^sopcsb jakéi mégvélasáíoÍi abol valamennyi gyim tovább sxubs^hxtáU lelhet I -3 R*í: sxabsaíáí^ssei; aaii; beoay ! Jjkboxolil; pT^liálbíaih: oxetasislh: €s-€y slcilMo, amely adott esetben sssuteöttóft. 1-5 R^ sxxäässöta^ssel; S- vagy 6- ttó téife vagy telSgign :g$Éríi amely 14;:heien5fefet tartalmaz. ahôttâÂÂyi gyl* .pi iésfr ssetevaÄSäsüi^i 1-3 En febxztRtfeeselj vagy 5- vagy b- Um í^mmmí$:0lié^;W0&amp; fefeh fspâfe.h phdiaddtótó pdtóR&amp;l gtfdtiuitâ, pirazmil, pirazoiil, iiazoKL tnaziml, tiadtazolil, oxazolil, ivoxazoül, iriazoiil, feüazolil tk>fe~2-il &amp; iAofe-3-ii csoportjából ntegváUtózioti, ahoi vatenaenoyi heteroaromás gyűti adott esetben szuhtóiiiáh 1 -3 R*' szubsztituetssseí: R24 jelentése H.. €·€* aikii, C; »€« aflfet, b®tó, vagy .tói, ahol valamennyi bénái vagy tói tóit esetben stórftóí 1-3 ΕΛ: méláimmá; R"'5 jelentése RCrCtókiK tóI vagy baml amely adod esetben sfetótuáli 1-3 R’* szahsztiíaenssel; R^jelenícse: II; Ci-C :s alkii; C-:-C-^ amoxi, tói stttek adott esetben szubszutuáli 1 -3 RA! stósfetótó; vagy 5- vagy 6 tagé heteroaromás gyűrő, amely furanü, piridimI p·femil-N-fed. pirimidmü, pirkfazinü, pirazind, tiazoUl. inától, tófeolil omzoíI, ttóoll éá fekazolif eseportlábéi meptfcÄb R”' és R ·' jelentése egymáséi tlggedenői:: Ff: Cä-€6alM; hefe!vagy fed, ahol vafefehyl beozii vagy :tó! tóti esetben szuhsáxmáll 1-3 írí: vtósstltoenssel; vagy % vagy $* tagö telkeit vagy telítetlen: gyöii, 'Midf 1-3 feetfeomoi tartannak, ahol valatnenayl gyűrő: adott esetben szubfetót 1 -3 R: ! szubsztituenssek tójefeiése: H; Cr-Q sikü: CrQhdoatkil; CVQi alkoxiaikih Cj-Cív aikilkarbond; benzü vagy fel, ahol valamennyi befel yagf?· fel tó% űsditó -igibsÄÄi 1-3 iP szubsztituenssel; vagy 5· vágyó- tagú telített vagy leUtetkn gyűrő, amely 1-3 b^ematomot takaim&amp;t, ahol valantennyi gyűrő adott esetben satótdíRiaR' 1-3 R*" SztófehaasSei; RSÖ jgfei&amp;e egyfestó! fogpiiettiflbalögiso, efep $ámy CrCs alkii, €1-13¾ MloalML ítós ibdiemaikb, Cb-Ch alhösdaikil, £34¾ hatoalkoxinlkil, ¢€-¾ alkenit €34¾ baifekend, € rfe alkiniL CrC* baloatóii tótól Cy 4¾ alkoxi, Ctó hatótól Cj-C* alkenüoxl CrQ* ható keni tój C-,-0, aldmlotü, Ç;-€* iniloalkiniioto, €-.-€fc aikiltvo, €rCg alkümdíbnil, C'A\ hak^alkilszaii'omi. ÙyCf, aleeaMo·,, €2-Q haloalkemltio,; <?arC* bafoalkenusxu! tonik C,-C« alkmiUto, €rO, ÄÄsmlfedk. CrO slkilamiuo. Cb-Cs d-alkdam.ino, QrO t|»Mi &amp;mJ. ptrimidinil vagy jűndik iêel a bagóik feil,: piridU, -vagy pMmMMI adott esetbe« xzubszüínák 1-3 RÄ! smbetóiuensssek Rn jelentése egymástól fűggeileaö.1 balogéit, ciano, nitro, C-% alkd, €Γ€* haioalkil, CrQ; ti#oxiaBol C. -C* alkcxialkü, C?-C, haioalboxialkd, : Gj-C,, dtebl, €,-¾ halMiteml, €yö> alkinil CrG* baloatkűűl, lűdroxik CrCyalkexk CrGyPtdoalkoxi:,; C2-C<; ÄÄIox^CrC« baloallcemloxi: €3:¾ alkíniioxt, 'Ùf€$. halöaMafed, €*-€« «Ikiltfc, O-O* alfcdmdíbmL CVC* ba!oa!kilsztdim«l (¾¾ alkemlbo, CjCUfeoaikeniliky €sC^loaÍtesi:i®^iÍbbtI, €3¾ glkMiío, €3¾ alkmilsztüíbnik CrQ, haloalkinilsmiiboiL CrO, alkilamloe, (€-<4 dialkilammo. C:>~C; dia;kiiammoksr boniI, vagy €.?-€* trialkikziril: R" jelentése egymástól függetlenül: űrCk alkil, C;4.'ii haloalkil, Cs-C, bidrosialkil, CrCj alkoxialkd, CrC, haktalkoxialkil, €?.-€* atoi, Cí-Cg baioalkeml, (.>€« slkmil, CrQ, laioaMïûk hidmxil, Í.QQ, aikoxi, €rÜbisdoajkexi, €rQ, álkeniioxi, €rQ haloalkenboxi, CrQ alkiniloxi, CQC* haloalkmüoxi, Q-Ü* alkiido, Cr€y alkíimdlbűil, € ; -€§ halo&amp;lkilsztdfonil, €;;··€;, alkenilbo, €->-Q teloalkenlliin, €>-€<, kdealkeniszuflenil, €3¾ aikinibo, 1¾¾ alkinilsaolimlk Cy-€§ Mealkimk^lfeni, €)4¾ aikiiamine, Csdilsdáalkilssdno, €j-€* ^sMiaMsokatboad, €5¾ irlälMlsxlld; tesil, Api a lend pürű adott esetben sg^sgiituáli 1,# Riy saebsxtitaesssel; vagy 5- vagy 4· tagó telített vagy lelketlen gyűrű, amely 1-3 heíeroatomot tartalmaz, ahol valamennyi gyűrű adott esetben sxubsztituáit 1-3 R:! sauhszíimettssei; Rn jelentése egymástól függetlenül: C:-€cí alkil €r€,s haloalkil, fertil vagy líetbL amely adott esetben szubsxtiíuál? í-3 R'y vzmsszbttsenssei vagy 3- vagy <>- tagé telített vagy telkeden gyűrű, amely 1 -3 heteroaíomot tartalmaz, ahol valamennyi gyűrű adott t^etb^ i-3 R!* sznbsstűuenssel; R^eietűése: €r€g alkif €:·-€<, kdealki, Úyú$ alkoxialkil, €;-€ft alkiiamlnet vagy 5- vagy ó- tage, telített vagy telítetlen gyűrű, amely 1-3 iefeoa|otpot tartalmaz, almi valamennyi gyn-rű adott esetben xzubazbtnáb 1-3 R! ! ^mbsziitoensseb: RJÍ jelentése: Cj-Cé alki, C2-€k alkdkarbmi.il; vagy 5- vagy 6- tagú telített vagy telítetlen gyűrű, amely 1-3 tóeroatonmi tartalmaz, ahol valamennyi gyűrű adott esetben s:mbsxíituá!í I -3 F.° szübssdltöensse!: R;'* jelentése Ä eíano, Ór€s aikii, alkoxi, häml t«gy feni, ahol valamennyi benxll vagy fedi adott esetben szsbsztidÄ 1-3 Rífí kádbaziituenssel;. akemsbv ttodon K® és R?w jelentése együtt: 5- vagy é- tagú télied agy telítetlen gyűrű, amely 1 -2 totecoatömot iatlateææ, atol váianiohöyl gyűrű adott esetben mibsztiíuált 1-3 R.” saohsatltaenssek és R>! jelentés© egymásai diggetlenül: E, halogén, vagy feni, amely adott esetién saubszdttolt í-S IG? smsbstodmnasel; €}·€«· ÄI, €;-€* haloalkil, hldrovil, €;-Q: äoxi, vagy Q<4 fcaWtai; vagy 5- vagy to tagú lelket vagy telítette* gyűrű, amely i -3 Itoetoatomnt tatlahnaa, atol valametatyl gyto ?i adoít esette sva-v** la wall 1~3 R:í sznbstotoestssel; a. snegszorhássai hogy a vegyidet nem 4*Mrà^54M^2-^Cî^rÂ^szilâfôxtipidn#îa, 2» emxi-'k-aasso-'S'-öam'glnmiilia vagy 2--atooxitoiSííöm-:S“íls0^irtoídln..where R! is -N (R ') R4; R? is <β ?; R? is H; R 1 is H; Rs is independently CrG. akii, C.4 '&amp; haloalkyl amoyo, a C-C * alkyl amine, is a diachamyl of CVG which is optionally a schematic or a 5- or 6-membered, unsaturated or unsaturated ring containing 1 to 3 heteroatoms, wherein each ring is optionally suffixed with 1-3 R 1! srtOsxtkieessei; I5: I have the price of this liver; I have: Imlogene, € rCs for alcohols, baloalkll, COOs «} co:: Cs- € s bsloGGxl, Ci-Cÿ alkyd, O; .¾ Mealklbk, snüri, GiRlgalkllamme, overmodel, CrOs alkoxlcarbonik or CgCk aMkaiéóntl; Rí!) Jeting jigsaw gaggle of Ilggetlenil bale, burial, ainy annno, ÜrG african, C> € Aikif, CeG whale !, COQ kdtoxia, Q.-C ^ alkonialld, GjRds / baloalkoxkffel, CrC * alkenib C ^ Gy Isloalkeall €> · · € <, gg báfoakinii hidrexib € rG, A <«á, CrOOkloalkop, 1¾ ^ ¾ slkenilox Cv- € * baloalkemloxi :: Hours * a! Ng, G3: Rly · 0 | alk | $% 0.! : Door & DoorMotorOt-Cémloalkisgulloni, CrC * albetycat Cj-Cs Mealketúko,: CrÓ | WoichemlxOiBníi C ^ Gs alkinylsil, CrG-v GiiráEgilosil !, C? O! slialkycarbonate, C ^ -Gs dlsMlapmocarbons, rQ, nickelcyclics, €;; ···> alkylcarbonyl, C trialkdsxisil, i-lysethoxyethylsulfonylsilylmethyl, phenyl, benOI, benxked, phenoxy, or 5- or 6-membered heteroaromatic rings , act valansensyl lead, benzyl, bessoxi, phenoxy. or 5- or 6 - nsgilTtTeRtItIon ring optionally sxnbMÜniÜ 1 -3 xtmbsxiksnesseL smefy one-way fegstlsnül l ff &amp; t tnegválasact 10! means CrGss aikd. € <- € * whale tksl; CrG4 alkenyl; C 1 -C 6 haloalkenyl; t äs s r st st st st p p p $ $ $ $ «« i i i i i i i i i i i i i i i i i i i i i i i i i i i i i CrC4 haloalkoxy fsdl, ru5lt, or tetrahydroquinolino, vdarnenny, optionally substituted with i-3R * ^ ubi, or (- CHro * Rs; -CHRm): ^ (0) ORsí (CHRî4> .ù ^ Û> R2% iCHR-4} ::: C (0} N (R27} R ^; • (CHRî4) ::: ORj <î; (CHR: î4} iy $ iÎS (CHR24):; ^ # 7) ^ • C (? 0} R?;; -? P5?)? -NR? X'b <bOR; '-: • Si (R \ _ -SO1Rr>; C2-C (: alRa-Roth; Gî-Cÿ: alRiïttmooRsrhool! : RC <; ilk ilk ilk l: l::::::::: M M M M ag ï ï ï ï ï ï ï ï Ô Ô Ô Ô ag ag ag ag ag ag ag ï ï vagy t t 5 5 Ô Ô Ô Ô ag ag ag ag ag ag ag xx, gkkxbdxml, pxidasxbl, | #what's &amp; my, xaaaa ;; Mpskil, tmdmaolik oppdÉ, xdagottl or Ipxaæegi. 0% &amp; given RS R® ^ bsaitaaBgsel; α m α -3 egesa Mam; W j & gt &nbsp; X% f &nbsp;H;balogel.;:Eiaxm;overwrite; CVC * alkyl: Ci &rdquo; : or nddl, mxxely given: vseitex saabkaid «hell 1-3 ll ^ sxebs iditttmssá:; €: - €,> -> Hydroxyalkyl-1 CrCo alkoxyalkyl; CrQ, haloalkiad; C; rCi, alkexdi; C; r-C * Ixateaikepxi ;; ·· (. ·, <. UÍívfe ': <C-rC's aîkcxi. C; - € ft haloaikoxi; C;' C. <. time *; CrQ aluOhoo; CyCh diazki lasmoo; OC. -Cs i'aíi sc'k; 'fromk'l'i :: no; Cr (' fc alkScarbom; Cj-Cfc ascicarboxyl; Cri '* acylamisocarbosyl; C.rCs dialksamazocarboyl; CrCetsâaiëkKlIil' coaddition itomaîmnâs ring, mxà and o, ji ji ji «ji ji ® ® o o 23 23 23 alf alf o alf alf a es es es es alf alf alf alf es es es es es es es es es es es es es es es es $ X-% axuk &amp;kltaebs;; or 5- or 6-membered heteroaromatic fruit »sdÿ plÂi» pMiSäÄali JtlfaÉl, plraziaih uaæoUl trkxinii, badiaxoll * 1 * 8, ix & yaaxÄ taanaobl & tıst whiteproof wb; H i-allogene; CrQu; Ct-C, haioalkii; CrQ, dk ararohio; return aînsîliy ad nsíhm s ^ ibsstimim 1-5 R "'* srabsæituei & sei b« öx) &amp; fssl: and bgkaoissída; fcà% ^ »ba» fesaa-2-yl «d-œotl-4iReopop: Jd> Jpirmb5-I, beb« ikaoR2'llybebzo {from "« 0'id s l uM mbaaol mei ^ ^ ^ -ji sopcsb Jake mégvélasáíoÍi testabol all Dima further sxubs ^ I may find hxtáU -3R * í: ^ sxabsaíáí ssei; aaii; beoay! Jjkboxolil; pT ^ lali baih: oxetasislh: € s- € y slcilMo, which may be sssuteöttóft. 1-5 R ^ sxxa; S or 6-th or telSgign: g $ Includes 14;: heien5fefet. ahôttâÂÂyi gyl * .pi iésfr ssetevaÄSi ^i ii 1-3 En febxztRtfeeelj or 5- or b- Um í ^ mmmí $: 0iL ^; W0 &amp; fefeh fspâfe.h phdiaddd pdtR &amp; gtfdtiuitâ, pyrazmyl, pyrazolyl, iiazocl tnaziml, thiadazolyl, oxazolyl, ivoxazoyl, iriazolyl, pheazolyl tk &gt; iAofe-3-ii, which is optionally substituted by a heteroaryl atom of the Vatenaenoyl heteroaromatic 1 R @ 3 R @ 1 = R @ 24 = * * alkyl, C; »€" aflfet, b®tó or .tói where all lame tó Toit case stórftóí 1-3 ΕΛ: méláimmá; R '' 5 is RCrCiOkKi or BamI, which may be spheroidal with 1-3 R '* saccharide, R 1 is C 1 -C 1 -C 6 s, alkyl, optionally C 1 - C 1-4 alkoxy; 3 Rothschools, or 5- or 6-membered heteroaromatic rings containing furanyl, pyridimylpemyl-N-coated pyrimidyl, fumarine, pyrazind, thiazolyl, pentafolyl omzo, toll and alpha-olefin R, R '' and R · 'stands for tlggedenő: Ff: Cä- € 6alM; hefe! or cover, where vafefehyl beozii or: in the case of suffusion, 1-3 writings: with vatosstltoens; or% or $ * member sites or unsaturated: germ,' Midf 1 -3fasphomol, where valatnenayl ring: optionally subfetor 1 -3 R: substituent has a H: Cr-Q cyano: CrQoalkyl; CVQi alkoxyalkyl C 1 -C 6 alkylcarbole; anti-glue-gigabyte with 1 to 3 iP substitutes; which is 1-3 bt ematomot takim &amp; t, where all the rings are optionally tufts RiaR '1-3 R * "StaphaneSei; RSÖ jgfei &amp; e is a one-color! toothbrush, effep $ iamy CrCs alkii, € 1-13¾ MloalML sparkling ibdiemaikb, Cb-Ch almonds, £ 34¾ hatoalkoxinlkil, ¢ € -¾ alkenes € 34¾ baifekend, € rfe alkiniL CrC * baloatorii Lake Cy 4¾ alkoxy, Cto Cj-C * alkenoxyl CrQ * is active in C -, - 0, aldmlotü, Ç; - € * iniloalkiniot, € -.- € fc timing, € rCg alchemybn, C'A \ t ÙyCf, aleeaMo ·, € 2-Q haloalkemtio ,; <? arC * bafoalkenusxu! tonic C, -C «alchemy, € rO, Ässmlfedk. CrO slkilamoje. Cb-Cs d-alkdam.ino, QrO t | »Mi &amp; mJ. ptrimidinyl or iêel iêel in their baguettes,: pyridU, or pMmMMI in a given case «xzubszínák 1-3 RÄ! smeltóiuensssek Rn stands for grass ggeileao.1 balogels, cyano, nitro, C% alkd, € Γ € * haoalkyl, CrQ; ti # oxiaBol C. -C * alkyloxy, C 1 -C 6, haioalboxialkd,: Gj-C ,, dtebl, €, -¾ halMiteml, € night> alkynyl CrG * balo-acyl, crude oxy CrCyalkexk CrGyPtdoalkoxi:,; C2-C <; SOUND ^ CrC «baloallcemloxi: € 3: ¾ alkíniioxt, 'Ùf € $. halafaMafed, € * - € «« Ikiltfc, OO * alfcdmdíbmL CVC * O! o! o! o! OST! (¾¾ alkemlbo; , (€ - <4 dialkylammon. C:> ~ C; dia; chamomoxyl boniI, or €. - € * trialkiriril: R "independently of one another: spaceCk alkyl, C4-4 haloalkyl, Cs-C, bidol , CrCj alkoxialkd, CrC, haktalkoxialkil, €? .- € * atoi, Ci-Cg baioalkeml, (.> € «slkmil, CrQ, levoMïûk hmxil, ÍQQ, aikoxi, € rHelpdeskxi, € rQ, false oxy, € rQ haloalkenboxi , CrQ alkynyloxy, CQC * haloalkoxy, Q-Ü * alkyd, Cr € y alkíimdlbűil, €; - € § halo & perilstfonil, € ;; ·· € ;, alkenylbo, € -> - Q teloalkenlin, €> - € < , kdealkeniszuflenil, € 3¾ alkinibo, 1¾¾ alkinyl salt glue Cy- € § Mealkimk ^ lfeni, €) 4¾ amine, Csdilsdáalkilssdno, € j- € * ^ sMiaMsokatboad, € 5¾ irlälMlsxlld; Riy sa or 5- or 4-membered saturated or unsaturated rings containing 1 to 3 heteroatoms, wherein each ring is optionally substituted with 1-3 R; sauhszíimettssei; Rn is independently of one another: C: - € title alkyl € r, and haloalkyl, fertil or letbL which is optionally subxtible? β-3 R'y is a ring or tertiary or saturated ring containing 1 to 3 heteroatoms, each ring having a tert-butyl radical; RH: € â € g Alkif €: â € <, kdealki, Uyu $ alkoxialk €; - € ft ali-amlnet or 5- or saturated, saturated or unsaturated ring containing 1-3 Ide-Ipo | ali all the guards are optionally xzubazbtnáb 1-3 R! ! [M + H] + = R 1 = C 1 -C 6 alkyl, C 2 -C 6 alkyl; or a 5- or 6-membered saturated or unsaturated ring containing 1 to 3 pt-aromatic radicals, where each ring is optionally s: mc. , alkoxyl, halogenated, wherein all benxlls or covers are optionally substituted with 1-3 Rifi tubs; akemsbv ttodon K® and R? w are taken together: a 5 or 5-membered winter brain unsaturated ring containing 1 to 2 totecat atoms, atol cyanoalkyl ring optionally substituted with 1-3 R. ”saohsatltaens and R>! Report © without each other: E, halogen, or fen, which is a case-by-case I-S IG? smsbstodmnasel; €} € € haloalkyl, hldrovil, € -Q: oxo or Q <4 fcaWtai; or a 5- or to-taged soul or saturated * ring that i-Itoetoatomnt tatlahnaa, atol has a low value of sva-v ** la wall 1 ~ 3 R: stsestestestest; the. snegsorhás: the chemical is not 4 * Mrà ^ 54M ^ 2- ^ Cî ^ r ^ silâfôxtipidn # îa, 2 »emxi-'k-aasso-'S'amam'glnmiilia or 2 - atooxitol .. 2. Az L igénypont szerinti 11) ítépietü vagyaiéi, ahol R:’ jelenése 11; R4 jelentése li R'V: jekntéss -CfeÖ)R'\ -Nto'tR*· κΛ -Sü:R'\ NR's€toÔK)RÎS, CrC. aMf €rfe altoxi ?i;" jelentése:H, Cí-€s alkil, Ry; jelentése €)-€&amp; alfái, lend, atol a feni atoll esetbe®. sztsbsxíűttái !-3 whMk\mmé, R” jetóése €rC6 alkit, feni! vagy lieml, amely afed esetbe® s;mbstoi«áli 1-3 Riö sznbsxtitnenssel, R?<í jelembe cérna, Crto alkil fent, atol a feni! altok esetbe« szubsxtduált 1-3 RM szabsxíinenssei, és Ri;' jelentése halogén, Cr-C* alkil, G-Ck altoxlThe property of claim 11 according to claim L, wherein R 1 'is 11; R4 is li R'V: Entry -CfeÖ) R'Nto'tR * · κΛ -Sü: R 'N' € toÔK) RÎS, CrC. aMf € rfe altoxi? i; "meaning H, Cí € s alkyl, Ry; meaning €) - € & alpha, fly, atol in the case of the atoll®. rC6 alkyd, tallen or lieml, which is afed® s; mbstoi «mystery 1-3 Riö sznbsxtitnens, R <<to the thread, Crto alkyl above, atol to the peninsula« subtxtured 1-3 RM, and Ri ; ' is halogen, C 1 -C 12 alkyl, G-Ck altoxl 3. Az. I. igénypont szerinti (!) képien! vagyaiét, atol E'jekEîëse ö; R4 j elemese H, R55 jelentése f-CflR-jsaR4!: m értéke 1., R"4 jelentése H, CrGt alkil, feni, R4" jelentése kondenzált totetoaromás gyűri, amely ben:toiofenI, kimlmil, tzokinoifel 1ΐαΐ0|2.,3^]ρτ^{;5 l-metil-l B~hesoP,3-elplmzoli, beaaoferműl és banzoimidazolil, 2,3--dihidm'-tommfeno-2~lf, 4mrtoi-4Sdieno[3,2·-bjpirsol-5~i,isádaae[!v2-a]piiidln~2”ü, ímidazotol fejüaxohfeil, benzotiazol-231, be®n«jbjti©fe«-7dl, b-ntod-dH-fedaaol-feil csoportjából megválasztott, atol valamennyi gyűrű adott esetben tovább szttbsxdítolt 1*3 sznbssz ttuenssel, Rí<5 jelentése halogén, &amp;··€* alkik Q ~G alkom.(3) according to claim 1! atol E'jekEîëse ö; R4 is element H, R55 is f-CfR-jsaR4: m is 1., R "4 is H, CrGt is alkyl, phenyl, R4" is a fused toteto aromatic ring wherein: thiophen, kimlmil, tzokinoifel 1ΐαΐ0 | 3 ^] ρτ ^ {; 5L-methyl-1B-hesoP, 3-elplmzol, beate-permol and banzoimidazolyl, 2,3-dihydm-tommfeno-2 ~ 1f, 4m-rt-4Sdd [3.2 · bjpirol] 5-i, isadate [? V2-a] pyridyl-2 ', suidazotol-headaxo-phenyl, benzothiazole-231, including? -Jd?,? -Dd, b-ntod-dH-fedaaol? optionally further diluted with 1 * 3 snb ttuens, R <<5 is halogen, &amp; 4. Az 1. igénypont szerintiit) képleté vegyűieí, atol R4 jelentése H; ^ jelentéseΉ, R44 jelentése (tolIRtoittR^·.: os értéke I, R.’4 jelentése M, RG jelentése S- vagy to tagú telített vagy tetlfeleo gyűrű, amely 1-3 teieroatonmt íartsdtnsx, atol valantennyi gyűrű adott esetbe® ssfesxümál i-3 Rn szabsztlmenssel.4. The compound of claim 1, wherein R 4 is H; 1, R44 is (tolirtoitR @ 1 = I, R.'4 is M, RG is a S- or to a membered saturated or tetl-ring which is 1 to 3 teertones at each occurrence, at each occurrence. 3 Rn with slider. 5. Az L igénypont szériád il) képletü vegynlei, atol R* jelentése H; R4 jelentése II, Ri; jelentése (-ÇMR^R",; m értéke 1, R"4 jelesstése H, jelentése 3- vagy ű- tagé heteeosromás gyűrű, atnely mraaü, pirldisűl, plmlmí-M-oxkly glnsnidtoL plndaarnll, piraaltil, pitnaoEI,. tiazoil, tnazinil tladlszólll, oxaaoiil, izorsmolll, triazolll, imldazold, ttofeiG-d és tiotox-3-11, i-metll-ll;l-pirazol-3-i:l csoportjából n^lasAliaW esetlen sxuésxijfeáb !-3 R3® ssnbsxtinjensse!, R^jéfeÂé "Μί$>φ*< iíbn, CrCt aifcrlv Cj-Cyaikoxi fe An L igénypnntsxfejati fi) képkM vegyülei, abnl Kijelentése B, Ru jelentése liAIHR^R2'’,: M értéke % jelentése S^,Aiís fstíl* m*â$&amp;ê&amp;n. esfeta safesxtituált 1-5 V?* ssfesxttfeenssel, R~' jelentése PafetL fenik amely aéleit esetlen safemitaátí "i~$ &amp;r sxubsxtifeeBxsel, R22 jeíestfese baingén, nitny €*-€4 alkli Gi;-€s a&amp;oxi, fernná, fenit, stri snéamsnnyi tooxl, feni . adott esetben. smteti&amp;Ä :1-3 sa&amp;bxaíltimnsxek amely egymástól jiggetlenö]; R*5 feni megvlfeystolt, irn jeteéése Italegétn €rG<, ajtó, Cs-C* Wôatt;be®àîÿ:|iliÂ5. The compound of formula L of formula L, atol R * is H; R4 is II, R1; denotes (-ÇMR 1 R ", m = 1, R" 4 denotes H, represents a 3- or 5-membered heteroaromatic ring, which is selected from the group consisting of pyrrole, p-methyl, oxynyl, pyridinyl, pynaole, thiazoyl, tnazin, t tladylol, oxaoyl, isormolll, triazolll, imidazold, ttofeiG and tiotox-3-11, i-methyl-11; 1-pyrazol-3-yl: nyl, unsaturated xxl, x 3 R 3 ssnbsxtinjensse, R ^ jéfeÂé "Μί $> φ * <libn, CrCt ifcclvlvjjjjjj Cy Cyaikaikleileileileileileileileileileileileileileileilei L L L L L L L L L L L L L L L L) )nnnnnnnnnnéseéseéseéseéseéseéseéseéseéseéseéseéseéseéseéseéseéseéseéseéseéseéseéseéseéseéseéseéseéseéseése ,ése Ru Ru Ru Ru Ru Ru Ru Ru Ru Ru Ru Ru Ru Ru Ru Ru Ru Ru Ru Ru Ru Ru:::: â € &amp; ê &amp; esfeta safesxtured with 1-5 Vs * ssfesxttfeens, R ~ 'stands for PafetL Phenomena, whose edges are clumsy safemate "i ~ $ &amp; sxubsxtifeeBxsel, R22 founder on baing, nitny * * - € 4 alk Gi; - € s & oxi, fernná, fenit, stri snéamsnyi tooxl, feni. in that particular case. smteti &amp; Ä: 1-3 sa &amp; bxailltimnsxek which is jiggle-free]; R * 5 feni vlfeystolt, irn jet roulette € rG <, door, Cs-C * Wôatt; be®àîÿ: ili 3, Αχ I. igénypont sxenmi (I) képleté vegyniet,ahol R' jelentése H; R4 jelentése H. jelentése (-€Μ!^%Ε*; m éneke I, R^ jelentése 1¾ R^ jMfekése saSi, benfe I ,3jéiMoii, feni, amely adok esetien sxabxgtifeâii 1 -5 R~v szfextituenssel, R*! jelentése halogén, eiano, nfero. afefe €rCA álfeiaíkfe €fÇ„ alkil, CrCk halna&amp;il CrQ-bidfetótó* OrCA atköálalkii feCk batoaltetatkil Cfe&amp;atketó, btdroxii €:fe alfei, feefeltfe, Cj-Cfe slkilstatifetäi, Gí-Cs alkilnnian, betfeífe fennxi afsel mlmmmm benyitó, í&amp;má áttol esetben sxfeRifeáft 1-3' sefefeegnfe,: afeeiy e|>a#st||:fî|ggetlénnl Kn kcMU ^steSft feVÍ jelentése fealogéfe CpCft alkíl, €§>*&amp; alkoxk R Αχ I « igénypont sxeonti Itt képlete: vegyifesèot 'W JÄÄ H; !G jelMiése 1I5: R" jelentése C-01I2ífel3Am értéke L lejelentése -OHfe -CHiCiR, -CiRCBvOfe beafe 4fen>fefe;R;;?'jelentése inti, 4-Íw-fefet, pAiit. f, Ax L igénypont sxakttó 0} képiéin vegpileí, ahellG jelentése II; R jelentése R R jelentés« (AltlpyGÁ ns éRéke 1, R23 jelenfese H, R:íí jelentése: fenik fsAotík 4-iuor~feniL 4~peto:xnfenil 3-tiofenfek iiofen-Mb 3*lí« a-feém-feniybe^ettötknl-íl 2,4J-tnm.eül-fenfe I -feRG-nfefexi-feni, 3A>enxoíntn|, 3-Ínor-4-s-etexkfefei Ιλ), Μ I tgenypoM sfenti # felet« oegyilek amely ax alábbi vegynletek fen! nnjgsmmsxtotL3, Αχ of formula I, wherein R 'is H; R4 is H. means (- € Μ! ^% Ε *; m song I, R ^ is 1¾ R ^ jMeSiSi, bene, 3jeiOiii, feni, which gives case sxabxgtifeâii 1 -5 R ~ v sxtxtense, R *! denotes halogen, eiano, nfero, rhp, rCA pseudo, alkyl, CrCk halon & CrQ-bidfeter * OrCA melting feCk batoaltetatkil betfeífe lixi afsel mlmmmm imprint, &amp; sxf sxfeRifea 1-3 'sefefeegnfe, afeeiy e |> a # st ||: f | | ggetlénnl Kn kcMU ^ steSft feVÍ means fealogéfe CpCft alc, € §> * & alcox R Igénypont I e sxeont The formula of the formula: is a compound of the formula 'W δ H'; G is a signal of 1 5 5: R ′ is C-01 I fel 2 β 3 Am of L is -OH CH -CHRCiR, -CiRCBvOfe beaf 4fen> fefe; R ;; Β-fefet, pAit. F, Ax L, sxct. 0} in vegpile, where G is II, R is RR report (AltlpyGa ns 1, R23 present) Case H, R 1i is: phenoxy fsotyl 4-fluorophenyl 4-peto: xnophenyl 3-thiophenophenophen-Mb 3 * 1? -phenol-phenyl; feRG-nfefexifen, 3A> enxointn |, 3-nor-4-s-etexkfefei Ιλ); nnjgsmmsxtotL Í L Készítmény gombé» patogésmk sæab%oxàséra, amely pmk&amp;m&amp;sb ae 1 ~10. igénypmáok bármelyike szerint! vegyükîeî. és fitoiôgtsüag. alkabaaaMé· hordozó anyagot,L For L Button »convenience button, which is pmk &amp; m &amp; sb ae 1 ~ 10. according to any requirements! vegyükîeî. and phytopharmaceuticals. alkabaaaMé · carrier material 12, AIL igénypont saedml készítmény,. aboi a gombás patogén alma vamsodás (Veumpla kaeqmfís), báza szeptóíiás feltosság (Septoría tribe;), cukorrépa cerknsporás foteség í'Cercospom betkok), íoldimogyorö cerkosporás foltosság (Cercospora aradridkola), ás fekete levélfoUossag (Myeospbaerelk fijkuois),12, AIL claim saedml preparation. aboi is a fungal pathogen apple obstruction (Veumpla kaeqmfís), basal septic fissure (Septoría tribe;), sugar beet cerknsporás l'Cercospom alphabet); 13, Eljárás gombás feAő^és szabályozására ás snegelózéséte növáoyekm, amely eljárás· tartalmazza azokat a. lépéseket, hogy legalább egy, az i -10, igéöypööiok. bármelyike szerint! vegyidet rimgkid hatású nmnnykéget kihord jak a mvé&amp;% a növény környezete, a növény fejlődését támogató talaj, a növény gyökere, a növény fevélzeie és a növény és valamely oka növény közül legalább egyik íemmsztésére alkalmas mag kezű! legalább az egyikre. 14, (ll képleté vegyidet alkalmazása Yi R1-" ' N 'R2 S ahol R' jelentése R: jelentése -OR-*: R'jelentése: hl; lYis:Ö; R8 jelentése egymástól mggetleoü! CrC«· alkií, Q -¾ hakalkíL ammo,. CrCL alMlamiro,, Q-Cí, dlafkiamiao, femksmely adott esetben sziíbsztifeálí L3 ΕΛ: szubsztitaenssek vagy 5- vagy 6- tagú íeMtett vagy telkeden gyűr«, amely $-0 tattalma^ ájfeol vakmgfmyl pürü «doit esetben sssfesatnuált 1-3 E!:i smbsetitneesgfet; 1;!? jelatóe. egymástól nlggettesÄ balogé«, €::-¾ alksk €]*$*> Mo$il§* CyC* atop, GKis báloslkoxi C?-C* álkíltlo, €}·*€§ hatealkikio, «mmo, €:;:-Cs ilMlamil®, %C* ÄN®, C2~€6 afexikarhímt!, vagy €;-€* aiytkagbölbl; IP jelentése egymástól Äs, ÄS, ambRy %-€<, slkopafed, CyCy sML; 0,-¾ baloaikil. CpCs hidroxialkü. Q-Cj alkoxiaiku. C. ~C\ haioalkoxsalkil €.»·€* alkeoil, C2«C4 bahalkeoiL €.*-€* alkuul. €*-€fc haíoalkimL hkteml C; *Cft aikoxi, CVC* halealkosi, Cj-Cs alkesltei, CyC\ haloalkeaüoxu cyC, alkiíűloxk CVC* haloalkinitoxi, CrQ, aikiltkx .CyCg balbálicíilöjCj'Cís »íMteü-iotsll, Cy€§ tebalkllszsíífééll €rCs alkemltky Cr<% baloaiiemltm, 1¾^¾ líaléaikesufe^ifos’óL: €r€* alktófe, Cj-Q alkimismlfonil, Ck~€s balóalkmilsáilídnü, Q'-C^ állImmM,; &amp;Ç* dlÄlatmno, cyö* álalMfemáíu>.kaíböni, :C2~£g alkexilmdpml, Ci-C* alkiksrbQuil,: CyCy· tmMlsmllL 2-||i)-'fueíoxijmtna|rM-mebkseeíaímdíí,: feml, bemál, bemsilexi &amp;ítöp:, ystgy 5» Wgy é- tagö betemammás gyám, aboi valamesmyi: :£eml;5 bénád, boaxboxi. Rpoxl yggy S* vagy b- tagi hemroaromäsipttm Md&amp;:miám. smbszSltostó 14 sxuteimnessel, amely egymástól SggeieMl R ': fedőül megválasztod; R:i jelentése: C . ~C-:4 íUklls C ;··€.;. baJoaíkik: C-:-C. aí kenik Q-C> haloaikemk CÆ alkuul; Cr€, hakmikinii; fenik naftík vagy íetmliidrokindmik, mlanteunyl adón esetben seubsaíimák 1-3 R4" sknbsssikvaíssel, 4€HRÍ4kEB; HCHR'^CtOlOR^; •(CMR í4)„;C(0)R ?íS; •n'3ílR;''b,4::(0)N(Rr;)R?’·; hSCHRm InvOR2“; kCi-ir'^sR"· 4C'llR;íb|aiN(R-7)R;:s; “C{~ö)R5í; -N-CCR^IíR-10): -N'r'C(-O}0R4S -SÍ(R?:.;;;; -SClR3'; CrCft alkoxikarbomi; CN alMlasÄokarhoni; C’j-Cn aikUkarbonü; énkor, mé$ mmÄ* Êxàim mégvilasxfett; vágy S- -m^é- tagé kemroaromas gyáré., amely 1¾¾¾. piódnii, gikÄli-M-ox»! pymMinll flÄÄl. ptaeMl pimxölilj itaxdllomadÄ üaÄaolil oxsxoiÜ, trlazolii vagy izosaïsoiil: csópóripbol megvá-ksæîc€:.Â)I véæœmÿï 5- vaig^ö-tagö^iöroaíomásgyörs a4öii«seib«ß xatlómttaáli 1-3H.** srabxztúuenssd; R~: jelentése egymástól mggetlesrül: m halogén; dans; diós; C;-(.\ aikií; CVC, haloaíkil; fedi vagy beméi amely adott esetben satedidák: 1-3 R' v szubszütuenssek CVQ hidroxialkil <rCl dfcoxilalkil; C>~C, isaloalkinil; ί\·~€1 alksml C;-C\. haloaikerui: C>~C, alkuéi 1· rGs alsoxi; C'i-C* haioaikoxi; CpCs aikiluo: C s -Cií alkilamíno; C ; ~€y diaiki lamiuo ; Cyí.\ dkmalk.il amin»; €V-C<;,. (alkilJcíkjoaMkítiiímt CrC;. aikilkarhottil Cy€é alkoxtkíóhooii; CyCg aMíatdnokarimnü; CrCg ddlkilsohookarhoinil; Iríaiklsdiik koßtedi kodrnammis gyim>: ixofemdmil iienotS^djpiridtl l- êii-bmmikmâmm megvfctd% atoí mtemennyi gyűrő tovihb sssáhsáómált fehet 1-3 ltí:5 ááóhskttineossel; vagy ..S* vágyé- îbranl, ptfkiflÉíy; pfeÂil-M'-mià, piriaúdiml, pmdazhid, plrazidsl, dazbli, Máztól, íiadrazoMI, özekűI, tóíxazotit iötteoSI 4β· t&amp;»ïi csoportjából megválasztod;; R"’ jdeoíése: H; halogén; CrC alkil; CrC„ halnaiki;. dialkiiamino: tkod, amely adott esetben, sztrbsxtduáit 1-5 RT4' szahsztitueossel; kondenzált heterosmmás: gyűrű, amely benzoiiofemk ktrmtód, ixokinolmií, ttómf2,Ko]plridiL 1~ mei.il-1 H-üenol^a-cjpirazoiil, beoxoíurató és benzolmklazold, 2 J-diÄo-tezöfesmS-ii, 4-metÜ-4H45ÂpJ4ï|pln:ô|-S-ïî, Jpfîàâdr^. heazötózei-tól, beijZ0|b|iibfe~?-il:5 és csöjf^ábéi ahol va* lametmyi gyűrő tovább sztbszttóáit lehat 1-3 Εΐβ sztMzttóenssd; nrtfUk fee&amp;zöf .1Mdioxeil; pirtóidinbbi;: Metaoit; CVC* alküt-o, airily adott esetben .sxnbsxütttót i-5 liW szttbsxtiíuenssel; S- vagy b- tagé telkeit vagy tóttetída gyűrű, amely !-3 betoroatomot tartalmaz, ahol vsíamermyt gyűrű acblt esetben szubsztituált í-3 Rn szubsztltaonssel; vagy 5- vagy 6- tagé heteroarootás gyünk amely furaoíL pirktód, ptridmil-N-oxid, pirímídirél, píridazűűL piraztól, pirazolîL, tiazolü, triazmii, tkidkuzolil oxazoUI, Izoxszobl, triazold. ímklazold, tkdkrtó-u és tioten-3-lí esoportjábó! megválasztott, ahol valamermyí heieroáromás gyűrő adott esetben szubsztitoájí 1-3 Κ:?υ szofetkuepssek Ri4 jelentése M, C--C.;. allét, Üi~£k alkosd, henzd, vagy load, ahol valametmyi beazd: vagy fend adott esetben sxubsztltuák 1-3 R‘:U szabszttteenssei; R< 3 jelentése H, Ct-€s alku, food vagy bemét, amely adott esetben szubszt-tuált 1-3 R*'! azűbaMmenssei;; Rf* Jelentése:: M; Cb-Ç,, alkll; CrC(i alkosd; lead, amely adott eMben sztfesMimli 1-3 R"'1 szubs/tnuensse!; s^agy 5- vagy 6 tágéheíet^snrás:gyűrű, amely ilsraod ptndűnk piridlnil-N-oxkl pinnddind, pindazüűl. píramol, bázelit, trlazMI, tladsazeldvoxazollb írkszolb és izexazolii esepot gébét megválasztott; S:2í és; m eAÄ; bestéi vagy tói, ahol vGamennyi beovil vagy Imi alól esetben srubszomálí 1-3 K.'” sssíkzílt«emsÉ'i vagy S~ vagy Ú~ tagi telitek; vagy telkeden gyűrő, «elv ;N3 beietóotoot tSdsta*% «hol valamennyi gyári adott esetben szobsxiítaált 1-3 lk! ' âzobstdMteossôl; R"'"'' jelentése: 1; CrOe slkib: C|-C- haioalkil; Mi alkopsÉék €-4¾ alkilfearhoali· berMi vagy fenik φ$ letó vagy fenil adott esetben smbsetkuáb 1-3 màmâmmsstâ; vagy 5- vagy o - tagú tellett vagy telítetlen gyűrő, amely l~3 beieroatomot tadaknnz, ahol valamennyi gyári adott esetben saahsatituáit 1-3 R!! saubsxdlnenssek R'H jeletdbse egymásról Rrgpilmnihdogfe, elaoo, nkro, €r€0 alkil, CVQ. haloalkl, Cr€* CSrC* »%0?d*Ä ßrG« MqMoxMkii CrCb alkenil, €2-€k Itóalfenik Cv-Cs alkhll, Cr€íi latotól, hidt»ki|,.€s-€si ;alkox| €)-€« Mmikoxi, €--€* alkentoi, C-tó haloalketósi, €3-C*: alkintoi Cí'Gs feitoltólexi, GrÜ;iÄitio, GrG;. alkilsmllbnii, Gr€* MoÂIsatâfôïti, Cj-C« alketkkio,: OrGkhatoatkeatlboy Otó* baloalkefelsmlfonil, Ca-C* alkiniliio, Ctós alkhtlsml&amp;ml, <*r Cs haMkinbsatktóh €*<&amp; alktlsmino:, €rCs dialkiarsloo, €.eCntókIaminokaiitól, (¾^¾ IjaMtol, tfeæoMk fel»· pMmidmh, vagy pmM* ahol a naaolil, :tól, pinbtl, vagy pMtókkt adod esetben, saabsvtimálí 1-3::$0 stótómonsssel; IGS jelentése egymástól igeimül balogén, ciáné, mm, €rCs alkil, -€r€§ haiealkil Citó fedmxmikli, C%CW stoxialki, ttóalkoxlalkíl, C;;-Ck elkenik G--C* fedostoki, Cy-G(i mkndi, Ctór baloalkkli, hidtmti, C:rGs alkosd, Cj-G* haloalkoxk CYCV alkemloxi,iG5'€s. baioaikeniloxi, €,-€< alkmlloxl, G;!-G*. daloaMnsloxi, CrC* alkiido, Cr< V tótólfenil CpCk hâloalkistoM, G--G$ alkemMö, CrGs fealealkeatltlo, Gi-€dbaioaikeni!ssultbolL ^.#11), Gr€§ atóltólfenlh €-4¾ haioalkinlsxatlboíi €**€$ altoxtók GVO* dialkiailao, €*»£$ dialklanittokaSŐtoml, vagy C-tó trialkllsktlih M;®jdmiése egyxtxéstól iiggetleaúl: €.·-€$ alkil, Cf-Gí, bnloalkil Cj-C* Mdtótók Ottó aikcxiaikií, €>~Q háloalkomaldl, GrC* alksml, 0.tó hatóktó, <&amp;«<&amp; atólb <#-<* hatótól, óidtól, Cj-Gs alkod, Ottó hatótok CrCi aikeniod, CrGö batóltótó €--0,. alkíniiexk €?·<·€ haioaiMnilod, 0,-(¾ aíkilio, Qtó áikitótól, €rCs IntloalkilsMlmnil, €;»>€*. aikenlhio, Cs-Cs-halosikeoItio, Cr€s €$*€« alktßilk*,. aMnils^lfösbl Cr% .McdfcÄgsltel, &amp;$*£&amp; €1-C» dtalkifammo, Ck-Cl àlaiyfeaànokarboîâl, CyC$ tnatkiistelrl;: ténü, ated afîoit jyüri adott esetben sxahsetlmálí 1-3 R* mthsMtwxmá;. vagy 5. vagy 6- tagú teiteílvsgv íelbeben gyári, amely 1-3 teteroatornot tartalmam ahol valamennyi győri adott esetben sxobsztituáií ! -3 R!' s>mbsztboeo.ssel; Krs jelentése egymásiós függetlenül: CrCö slkil €:-€* haioalkii, fenil vagy berni amely adott esetben ssmbsztuuált 1-3 R:w sssíbs2:tittíen$sel; vagy 5- vagy b- tagú tel tett vagy telítetlen gyünk amely 1-3 hetematomot tartalmam ahol valamennyi gyű ri adott esetben szufesÂ*àlt 1-3 RSi sïætetnaenssei;; K vï jelentése: Cr€;i alkil, Ci-C6 haioaiksl. Cr£* aikoxialkll tukilamino; vagy 3- vagy 6- tagú telted vagy telítetlen gyünk amely 1-3 heteroatomot tartateaa, ahol valamexmyí gyúrd adott esetben szubsvtteáíi 1-3 R :S ssrobseí-tneassel; Kijelentése: CrQi alkil, QrQ. aikilk&amp;rbonil; vagy g» vagy #- tap telített vagy tel teden gyűrű, amely 1-3 Éetemsimmtí.' imtahmz, aboi valamermyi piai adott esetben yxtibsztäuiiit 1-3 R!ï smb®$itomm^: jelentése II cíana, CVQ siál CKo afexk b&amp;ml* vagy Ipák abol valamennyi bemül vagy fern! adott esetben spbgpmáli 1-3 Rf vaobsetltttenssel; alternativ #1¾ Ríií: # E:'* jelentése együtt: 5- vagy 6- tágn telített vagy teliében .gyűrő, amely 1-3 beteroatontoi tpalpam aboi valamennyi gfű~ ri adott esetbeivsnofesgtltnllt 1-3 EíS spbstetoerpeiés &amp;* '' jelentése egymástól Elgpifgnüi: 1¾ balogén, vagy tetei, amely adott esetben saefesteteáb 1-3 ESö spfesztiuenssel CrCft aiál -0(-¾ Ibioalkil Mároxik CrQ alkom, vagy Q-€* iajoalkexk: vagy 5- vagy 6- tagi telteti vagy telteden gyárik amely 1-3 betet Oatomór imabsam abol vteamemp gyűrű adp esetbe® sznfosPteati 1-3 Ru smtbsatinensae!; egy növény gombás patopn által történő megíettőaésámk mepkadalyotesara.13, a method for controlling fungus and regulating it and snegeling it, which process includes a. steps to make at least one, i-10, come to mind. any one! the chemical environment rimgkid-effect nylon is thrown out of the plant environment, the soil supporting the plant's development, the root of the plant, the herbaceous plant and at least one of the plants and the cause of the plant can be seeded! at least one. 14, (use of formula II as Yi R1- '' N 'R2S where R' is R: is -OR- *: R 'is as follows: hl; lYis: Ö; R8 is mggetleo! CrC? ¾ hakalkíL ammo, CrCL alMlamiro ,, Q-Ci, dlafkiamiao, any of which may be siphilic L3 ΕΛ: substitutes or 5- or 6-membered or ringed ring, which in the case of $ -0 tampons ol vak m m m m m m oit oit oit oitoit -3 E!: I smbsetitneesgfet; 1;!? Signator. NlggettesÄ balogé «, € :: - ¾ alksk €] * $ *> Mo $ il§ * CyC * atop, GKis whalexx C? -C * } · * € § hatealkikio, «mmo, €:;: - Cs ilMlamil®,% C * ÄN®, C2 ~ € 6 afexicarhim !, or €; - € * aiytkagbölbl; IP stands for Äs, ÄS, ambRy% - € <, slkopafed, CyCy sML; 0, -¾ baloaikil. CpCs hydroxyalkyl. Q-Cj alkoxy. C. · C haioalkoxsalkil €. - € fc haoalalkim hkteml C; * Cft alkox, CVC * halealk, Cj-Cs alkeslite, Cy Haloalkyloxy cyC, alkyloxyls CVC * haloalkinitox, CrQ, aikiltkx. C 1 -C 10 alkynylfonyl, C 6 -C 10 alkynyl maleate, Q'-C 1-10 mmM; &amp; Ç * dlÄlatmno, cikk * mfemáí> .kiii,: C2 ~ gg alkexilmdpml, Ci-C * alkiksrbQuil,: CyCy · tmMlsmllL 2- || i) - 'fueíoxijmtna | rM-mebkseeíaím tolli: feml, dip, bemsilexi &amp; Judge,, ystgy 5 »Wgy em ás ás ás ás,,, oi oi oi oi oi oi oi oi oi oi oi eml eml eml eml eml eml eml eml eml Rpoxl yggy S * or b- tag hemroaromäsipttm Md &amp;: my. smbsztltosto 14 sxuteimnes, which are separated by SggeieMl R ': cover; R 1 is C. ~ C-: 4 liters C · · €.;. baJooms: C -: - C. ai can Q-C> halo Ck at the beginning of the night; Cr €, hakmikinii; phenolic naphthic or cyclohexyl, mlanteunyl transmucosal compounds 1-3 R4 "with scintillation, 4 € HR4kEB; HCHR1C4O1O4; (CMR4)"; C (O) R11S; • n'3lR; 'b, 4: :( 0) N (Rr;) R? '; HSCHRm InvOR2;' kCi-and '^ sR' · 4C'llR; βb αN (R-7) R; "C {~ ö) R5i; -N-CCR1-R10-10): -N'r'C (-O} 0R4S-Si (R '; ;;;; -SC1R3'; CrCl3 alkoxycarb; CN alMlasCarmon; C'-Cn alkUcarbonyl; , ye $ mm * àxàim stillvilxfett; desire for a S-m ^ member of a chemoaroma factory, which has 1¾ ž¾ pectin, glycol-M-oxypyrimine, ptaeMl pimxylleatexyladoxazol, oxazole, trlazolite or isosaicol: chopper. €: .Â) I am a 5-membered compound of the formula: 1-3H. ** The radicals are as follows: m is halogen: m halogen, dans; walnut; C- (. \ T alkyl, CVC, haloalkyl, cover or inputs optionally satedid: 1-3 R 'v subtens CVQ hydroxyalkyl <rCl dfloxylalkyl, C> C, isaloalkyl; C ~ CCil haloalkoxy; CpsC *alkyl: C s *Cialkylamino; C; € y y diaiki; (alkylcycloacetate, CrCl; n-α; or ..S * desire- îbranl, ptfkiflÉíy; pfeÂil-M'-mià, piriaudiml, pmdazhid, plrazidsl, dazbli, mázt, adiadrazoMI, widowI, lakexazotit iötteoSI 4β · t &amp;ïi; R '' jdeolation: H; halogen; C 1 -C 6 alkyl; CrC 'halo; dialkiamino: tk, optionally substituted with 1-5 RT 4' condensate; condensed heterocyclic ring containing benzoyl phenol, ixoquinol, ttomof 2, Ko] plidid 1 meiyl-1H-enenol-α-cispyrazolyl, oxoureate and benzene mucilage, 2J-di-thiohephorm-η, 4-methyl-4H45 βJ4ï | pln | | -S-ïî, Jpfîàâdr ^. | b | iibfe ~? -il: 5 and dummy alphabet where va * lametmyi ring can be further classified as 1-3 Εΐβ sttzmt; nrtfUk fee &amp; ff .1Mdioxeil; more phthalide ;: Metaoit; CVC * alkyd-o, airily optionally. sxnbsxcomputer with i-5 liW patchy; S- or b-tagged or ring-filled ring containing β-betoro atom, where γ-amylmyl ring is substituted with β-Rn substitution by acblt, or 5- or 6-membered heteroarotic ring, which is odd buyer, ptridyl-N-oxide, pyrimidyl, pyridyl, pyrazole, pyrazole, thiazole, triazmiole, tkidazole xazoUI, Isoxyl, triazole, cosmic acid, tkdct-u and thioten-3-yl. selected, wherein any hybrid radical ring is optionally substituted with 1-3 Κ: ??? allele, Üi ~ £ k, hen, hen, or load, whereby any beazd: or possibly sxubststtu 1-3 R ': U standard; R <3 is H, Ct- € s bargain, food or input, optionally substituted with 1-3 R * '! azűbaMmenssei ;; Rf * Meaning :: M; Cb-C11 alkyl; CrC (i.e., i.e., a derivative of m.p. 1-3 R @ 1 in s), 5 or 6 broad rings: ring containing pyridyl-N-oxcapddindyl; chelel, trlazmi, tladsazeldvoxazollb irbazoli and izexazolii esepot gebe; s: 2i and; m eAÄ; or full-ring, «principle; N3 insertion product Sdsta *%« where all the factory optionally has been scaled-down from 1-3 pp. âzobstdMteoss; R "'' 'means: 1; CrOe slkib: C 1 -C 6 haloalkyl; What is an alcohols € -4¾ alkylearcoal or phenol, or phenyl optionally smbsetu in 1 to 3 m, or 5- or o-membered, unsaturated or unsaturated ring, each having 1-3 carbon atoms, each optionally substituted with 1 to 3 carbon atoms; 3 R !! saubsxdlnenssek R'H sign for each other Rrgpilmnihdogfe, elaoo, nkro, € r € 0 alkyl, CVQ. Haloalkl, Cr € * CSrC * »% 0? D * Ä ßrG« MqMoxMkii CrCb alkenyl, € 2- € k Coco Cubic Chalks, Cr € Price, cold »out |, € €; alkoxyalkanoic | €) - € Mmicox, € - € * alkentol, Lake C haloalket, € 3-C *: Cí'Gs feitoltólexi, GrÜ; iÄitio, GrG ;. alkylmllbnii, € * MoÂIsatâfôïti, Cj-C «alkyd,: OrGkhatoatkeatlboy Otto * baloalkefelsmlfonyl, Ca-C * alkynyl, Ctós alkhtlsml &amp; ml, <* r Cs haMkinbsatktóh € * <&amp; altlsmino :, € rCs dialkiarsloo, € .eContentsIminokai, (¾ ^ ¾ IjaMtol, tfeæoMk up »· pMmidmh, or pmM * where you give naaolil, from, pinbtl, or pMtokk, in case you get a 1-3 :: $ 0 stack; IGS meaning cylindrical, cyan, mm, € rCs alkyl, - € rh § § haiealkil Citroximmyclics, C% CW stoxialk, tolkoxylalkyl, C; - Ck elk G - C * cover, Cy-G (i mkndi, Ctori) baloalkyl, cold, C: rGs alkosd, Cj-G * haloalkoxk CYCV alkemloxi, iG5' € baioaikeniloxy, €, - € <alkmlloxl, G;! - G *. daloaMnsloxi, CrC * Alkoid , G - G $ alemMo, CrGs fealealkeatltlo, GI € dbaioa ssultbolL ^. # 11), Gr € § from aflhl € -4¾ haioalkinlsxatlboí € ** € $ altoxtok GVO * dialkiailao, € * »£ $ dialklanittokaSÕtoml, or C tó trialkllsktlih M; jjdmije iiggetlig: €. · - € $ alkyl, Cf-Gí, bnloalkyl Cj-C * Mdtotok Ottó aikcxiaikií, â € oQ Queue comedy, GrC * alksml, 0.power, <&amp; « <& a mp; atl <<- <* from active, from, Cj-Gs, Otto, CrCi aikeniod, CrGö batto € --0 ,. alchemy €? · <· € haioaiMnilod, 0, - (¾ aíkilio, from Qtó farmer, € rCs IntloalkilsMlmnil, €; »€ *. alkenlich, Cs-Cs haloicio, Cr € s € $ * €« alktßilk * ,. aMnils ^ lfösbl Cr% .McdfcÄgsltel, &amp; $ £ &amp; € 1-C? -dalalkammo, Ck-Cl? or a 6-membered tea plant with a content of 1 to 3 teteroatornotes, each of which is optionally sxobstable! -3 r! s> mbsztboeo.ssel; Krs stands for each other: CrCö slkil €: - € * haioalkii, phenyl or Bern optionally spliced with 1-3 R: w sssíbs2: tittin $ sel; or a 5- or b-membered or unsaturated ring containing from 1 to 3 hetamomites, wherein each collector is optionally sufessionally 1-3 RSi; K vï means Cr, ialkyl, C1-C6 haloalkyl, Cr £ *alkoxyalkyl forylamino, or 3 or 6 membered unsaturated or unsaturated clays k is 1 to 3 heteroatoms wherein valamex is optionally substituted with 1-3 Rs: ssrobse-tneassel; Statement: CrQi alkyl, QrQ. alkyl &amp;carbonyl; or g »or # - tap saturated or tel teden ring, which is 1-3. imtahmz, aboi iptiy psi yxtibsztäuiiit 1-3 R! ï smb® $ itomm ^: meaning II title, CVQ sphere CKo afexk b &amp; ml * or Ipos abol all in or fern! optionally with 1-3 Rf spbgppm; alternate # 1¾ Ríi: # E: '* means together: 5- or 6-dimensionally saturated or full. ring, which is 1-3 beteroatonotopespalpam aboi each gf ri adott 3 3 3 3 3 3 3 3 3 3 3 3 3 jelentése jelentése Elkpifgnüi: 1¾ balogen, or tops, which may be sawn timber, 1-3 Cubic zinc CrCft -0 (-¾ Ibioalkyl Macro CrQ, or Q- € * iajoalkexk: either 5 or 6 member tent or telted factory 3 inserts Oatomic imabsam abol vteamemp ring adp caseStfatPteati 1-3 Ru smtbsatinensae; a plant fungus patopn, and mepkadalyotesara.
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